2-Pyrazinecarboxylic acid → HCID 69269313, compound

HRID 751542Notes

Reaction equation

HRID 751542 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[C:3]=1[C:11]1[C:12](=[O:32])[NH:13][C:14](=[O:31])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:17]=1.C(N(CC)CC)C.[N:40]1[CH:45]=[CH:44][N:43]=[CH:42][C:41]=1[C:46](O)=[O:47].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[C:3]=1[C:11]1[C:12](=[O:32])[NH:13][C:14](=[O:31])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH:25]2[CH2:26][CH2:27][N:28]([C:46]([C:41]3[CH:42]=[N:43][CH:44]=[CH:45][N:40]=3)=[O:47])[CH2:29][CH2:30]2)[CH:17]=1

Participants

8

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69267725HCID 69267725, compound

Product 1

HCID 69269313HCID 69269313, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-(6-Fluoro-2,3-dihydrobenzofur-7-yl)-4-[1-(piperidin-4-yl]-1H-indol-3-yl)pyrrole-2,5-dione (180 mg, 0.42 mmol) in dimethylformamide with triethyl amine (0.2 mL, 1.4 mmol), 2-pyrazinecarboxylic acid (57 mg, 0.46 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimid hydrochloride (106 mg, 0.55 mmol), and 1-hydroxybenzotriazole (74 mg, 0.55 mmol). Stir the reaction mixture at ambient temperature for 18 hours. Dilute with ethyl acetate, and wash the organic layer with water/brine (×4). Dry over magnesium sulfate and concentrate. Purify by chromatography (silica gel; hexane/EtOAc; 1:1 to 0:1) to give an orange solid (105 mg, 49%). MS (MSI) m/z 538 (M+H)+.

Workup

  1. washwash the organic layer with water/brine (×4)
  2. dry with materialDry over magnesium sulfate
  3. concentrationconcentrate
  4. customPurify by chromatography (silica gel; hexane/EtOAc; 1:1 to 0:1)

Sources & evidence

ORD record
ord-8f2cefdf076e423ebf9e59d771ad4c79
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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