Pyrazinamide
货号 B1679903
:
98-96-4
分子量: 123.11 g/mol
InChI 键: IPEHBUMCGVEMRF-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US06809099B2
Procedure details
Diethylaniline (0.33 μL, 2.1 μmol, 1.1 equiv) was added in one portion to a stirred solution of the amine (1.0 mg, 1.9 μmol, 1 equiv) in THF (0.2 mL) at 0° C. under an argon atmosphere and the solution was stirred for 5 min. 2-Pyrazinecarboxylic acid (0.31 mg, 2.5 μmol, 1.3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.48 mg, 2.5 μmol, 1.3 equiv) and 1-hydroxybenzotriazole (0.31 mg, 2.3 μmol, 1.2 equiv) were then added separately, each in one portion, to the above solution at 0° C. The reaction mixture was warmed to 23° C. over 17 h 40 min, then was quenched with saturated aqueous ammonium chloride solution (3 mL). The mixture was diluted with ethyl acetate (10 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layer was dried over sodium sulfate. Concentration in vacuo left a white solid, which was purified by flash column chromatography (80% ethyl acetate-hexanes) to give the pyrazine-2-carboxylic acid amide derivative (1.1 mg, 92%) as a white solid.
[Compound]
Name
amine
Quantity
1 mg
Type
reactant
Reaction Step One
Quantity
0.48 mg
Type
reactant
Reaction Step Two
Yield
92%
Identifiers
|
REACTION_CXSMILES
|
CC[N:3](C1C=CC=CC=1)CC.[N:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[C:18]([OH:20])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C1COCC1>[N:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[C:18]([NH2:3])=[O:20] |f:2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0.33 μL
|
|
Type
|
reactant
|
|
Smiles
|
CCN(CC)C=1C=CC=CC1
|
[Compound]
|
Name
|
amine
|
|
Quantity
|
1 mg
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0.2 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Two
|
Name
|
|
|
Quantity
|
0.31 mg
|
|
Type
|
reactant
|
|
Smiles
|
N1=C(C=NC=C1)C(=O)O
|
|
Name
|
|
|
Quantity
|
0.48 mg
|
|
Type
|
reactant
|
|
Smiles
|
Cl.CN(CCCN=C=NCC)C
|
|
Name
|
|
|
Quantity
|
0.31 mg
|
|
Type
|
reactant
|
|
Smiles
|
ON1N=NC2=C1C=CC=C2
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
23 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the solution was stirred for 5 min
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
at 0° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was quenched with saturated aqueous ammonium chloride solution (3 mL)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
The mixture was diluted with ethyl acetate (10 mL)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the layers were separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The aqueous layer was extracted with ethyl acetate (10 mL)
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
the combined organic layer was dried over sodium sulfate
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
Concentration in vacuo
|
WAIT
|
Type
|
WAIT
|
|
Details
|
left a white solid, which
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was purified by flash column chromatography (80% ethyl acetate-hexanes)
|
Outcomes
Product
Details
Reaction Time |
5 min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
N1=C(C=NC=C1)C(=O)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 1.1 mg | |
| YIELD: PERCENTYIELD | 92% | |
| YIELD: CALCULATEDPERCENTYIELD | 425.5% |
Source
|
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. |
