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

HRID 1428099Notes

Reaction equation

HRID 1428099 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:31])[C:19]([C:28](O)=[O:29])=[CH:20][N:21]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:22]=2)=[CH:13][CH:12]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.[NH2:59][C:60]1[CH:65]=[CH:64][C:63]([C:66]2[C:67]([NH2:73])=[N:68][CH:69]=[C:70]([Br:72])[CH:71]=2)=[CH:62][CH:61]=1>CN(C=O)C.O>[NH2:73][C:67]1[C:66]([C:63]2[CH:62]=[CH:61][C:60]([NH:59][C:28]([C:19]3[C:18](=[O:31])[C:17]([C:14]4[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=4)=[CH:22][N:21]([CH2:23][C:24]([F:26])([F:25])[F:27])[CH:20]=3)=[O:29])=[CH:65][CH:64]=2)=[CH:71][C:70]([Br:72])=[CH:69][N:68]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 682889763-(4-Aminophenyl)-5-bromopyridin-2-amineHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 867000505-(4-Fluorophenyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 86700049N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-5-(4-fluorophenyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydropyridine-3-carboxamideYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (414 μl) was added to a solution of the compound obtained in Step 2 of Example 9 (500 mg) and COMU (883 mg) in DMF (8.0 ml) at room temperature, and the mixture was stirred for 25 minutes. The compound obtained in Step 1 of Example 1 (440 mg) was added at room temperature. The mixture was stirred for 19 hours, followed by the addition of water. The precipitated solid was collected by filtration, suspended in chloroform/diisopropyl ether and then collected by filtration to give 800 mg of the title compound.

Workup

  1. stirringThe mixture was stirred for 19 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e7de9642c0cb4c41a951320a01d92bba
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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