REACTION_CXSMILES
|
C[O:2][C:3]([C:5]1[C:14]([NH2:15])=[C:13]([F:16])[C:8]2[N:9]=[CH:10][N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:23][C:24]1[CH:29]=[CH:28][C:27](I)=[C:26]([Cl:31])[CH:25]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C1(OC)C=CC=CC=1.CO>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([NH:15][C:14]2[C:5]([C:3]([OH:2])=[O:4])=[CH:6][C:7]3[N:11]([CH3:12])[CH:10]=[N:9][C:8]=3[C:13]=2[F:16])=[C:26]([Cl:31])[CH:25]=1 |f:1.2.3,6.7|
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Name
|
|
Quantity
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20 mL
|
Type
|
solvent
|
Smiles
|
C1(=CC=CC=C1)OC
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Name
|
|
Quantity
|
8 g
|
Type
|
reactant
|
Smiles
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COC(=O)C1=CC2=C(N=CN2C)C(=C1N)F
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Name
|
cesium carbonate
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Quantity
|
22.48 g
|
Type
|
reactant
|
Smiles
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C([O-])([O-])=O.[Cs+].[Cs+]
|
Name
|
|
Quantity
|
76 mL
|
Type
|
solvent
|
Smiles
|
C1(=CC=CC=C1)OC
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Name
|
|
Quantity
|
1.6 g
|
Type
|
reactant
|
Smiles
|
BrC1=CC(=C(C=C1)I)Cl
|
Name
|
|
Quantity
|
0 (± 1) mol
|
Type
|
reactant
|
Smiles
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COC(=O)C1=CC2=C(N=CN2C)C(=C1N)F
|
Name
|
|
Quantity
|
40.99 mL
|
Type
|
reactant
|
Smiles
|
S(O)(O)(=O)=O
|
Name
|
|
Quantity
|
10.25 mL
|
Type
|
reactant
|
Smiles
|
S(O)(O)(=O)=O
|
Name
|
|
Quantity
|
5.46 g
|
Type
|
reactant
|
Smiles
|
[OH-].[Na+]
|
Name
|
|
Quantity
|
24 mL
|
Type
|
solvent
|
Smiles
|
CO
|
Name
|
ester
|
Quantity
|
0 (± 1) mol
|
Type
|
reactant
|
Smiles
|
|
Control Type
|
UNSPECIFIED
|
Setpoint
|
100 (± 2) °C
|
Type
|
CUSTOM
|
Details
|
with stirring at 350 rpm
|
Rate
|
UNSPECIFIED
|
RPM
|
0
|
Conditions are dynamic
|
1
|
Details
|
See reaction.notes.procedure_details.
|
Type
|
CUSTOM
|
Details
|
The preformed catalyst, as prepared above,
|
Type
|
ADDITION
|
Details
|
was then added to the mixture
|
Type
|
CUSTOM
|
Details
|
to provide a dark brown suspension, which
|
Type
|
TEMPERATURE
|
Details
|
The reaction mixture was cooled to about 80° C.
|
Type
|
WAIT
|
Details
|
Gas evolution was observed after 10 minutes
|
Duration
|
10 min
|
Type
|
ADDITION
|
Details
|
the rate of addition
|
Type
|
ADDITION
|
Details
|
At the end of the addition the pH was between 7 and 8
|
Type
|
CUSTOM
|
Details
|
to give mobile slurry with a pH of 0
|
Type
|
FILTRATION
|
Details
|
filter agent
|
Type
|
ADDITION
|
Details
|
was added
|
Type
|
FILTRATION
|
Details
|
It was then filtered at about 80° C. through a water-wet pad of Celatom FW-14
|
Type
|
FILTRATION
|
Details
|
filter agent
|
Type
|
WASH
|
Details
|
the cake was washed with anisole (1×40 mL+3×20 mL)
|
Type
|
CUSTOM
|
Details
|
The lower aqueous layer was separated
|
Type
|
WASH
|
Details
|
the organic layer was washed with 10% aqueous NaCl solution (2×40 mL)
|
Type
|
TEMPERATURE
|
Details
|
the mixture was heated at 65° C.
|
Type
|
STIRRING
|
Details
|
with stirring
|
Type
|
TEMPERATURE
|
Details
|
the slurry was cooled to 15° C.
|
Type
|
FILTRATION
|
Details
|
filtered on a sinter
|
Type
|
WASH
|
Details
|
The solid was washed with water (4×24 mL), MTBE (24 mL), and acetonitrile (2×25 mL)
|
Type
|
CUSTOM
|
Details
|
dried at 45° C. in a vacuum oven
|
Reaction Time |
41 h |
Name
|
|
Type
|
product
|
Smiles
|
BrC1=CC(=C(C=C1)NC=1C(=CC2=C(N=CN2C)C1F)C(=O)O)Cl
|
Type | Value | Analysis |
---|---|---|
AMOUNT: MASS | 11.07 g | |
YIELD: PERCENTYIELD | 72.2% | |
YIELD: CALCULATEDPERCENTYIELD | 569.1% |
Source
|
Open Reaction Database (ORD) |
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |