2-Pyrazinecarboxylic acid → HCID 67443458, compound

HRID 1800879Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:29]2[C:38]([CH3:40])([CH3:39])[CH2:37][C:36]3[C:31](=[C:32]([C:42]([OH:44])=[O:43])[CH:33]=[C:34]([Cl:41])[CH:35]=3)[NH:30]2)[CH:26]=[CH:27][CH:28]=1>CN(C)C=O>[Cl:41][C:34]1[CH:35]=[C:36]2[C:31](=[C:32]([C:42]([OH:44])=[O:43])[CH:33]=1)[NH:30][CH:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([NH:22][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[O:9])[CH:24]=1)[C:38]([CH3:40])([CH3:39])[CH2:37]2

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of pyrazine-2-carboxylic acid (0.412 g, 3.3 mmol) and 1,1′-carbonyldiimidazole (0.7 g, 4.3 mmol) in N,N-dimethylformamide (10 mL) was stirred at 70° C. for 1 h. A solution of 2-(3-amino-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (0.75 g, 2.3 mmol) in N,N-dimethylformamide (5 mL) was added and the mixture was allowed to stir at 25° C. for 1 h. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 6-chloro-3,3-dimethyl-2-{3-[(pyrazine-2-carbonyl)-amino]-phenyl}-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (228 mg, 15%) as a light yellow solid: LC/MS m/e calcd for C23H21ClN4O3 (M+H)+: 437.90, observed: 437.1.

Workup

customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

Sources & evidence

ORD record: ord-1f882a7c47bf4263afb7d765275857b3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344137B2

Reaction notes

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