Diisopropylethylamine → N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-1-ethyl-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide

HRID 1428110Notes

Reaction equation

HRID 1428110 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]3[C:31](=[O:32])[C:30]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:29][N:28]([CH2:40][CH3:41])[CH:27]=3)=[O:25])=[CH:19][CH:18]=2)=[CH:15][C:14](C2C=CC(OC)=C(OC)C=2)=[CH:13][N:12]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.NC1C=CC(C2C(N)=NC=C([Br:92])C=2)=CC=1>CN(C=O)C.O>[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]3[C:31](=[O:32])[C:30]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:29][N:28]([CH2:40][CH3:41])[CH:27]=3)=[O:25])=[CH:19][CH:18]=2)=[CH:15][C:14]([Br:92])=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 682889763-(4-Aminophenyl)-5-bromopyridin-2-amineHCID 71660811N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-1-ethyl-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamideHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate

Product 1

HCID 86700063N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-1-ethyl-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamideYield 242%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (120 μl) was added to a solution of the compound obtained in Step of Example 3 (80 mg) and COMU (192 mg) in DMF (1.5 ml) at room temperature, and the mixture was stirred for 10 minutes. The compound obtained in Step 1 of Example 1 (100 mg) was added at room temperature. The mixture was stirred for four hours, followed by the addition of water. The precipitated solid was collected by filtration to give 174 mg of the title compound.

Workup

  1. stirringThe mixture was stirred for four hours
  2. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-76b689fb31134481b6681518f1f31943
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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