Diisopropylethylamine → 4'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]biphenyl-2-carboxamide

HRID 1524005Notes

Reaction equation

HRID 1524005 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:29](O)=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][C:18]=2[F:32])=[CH:13][N:12]=1.[F:33][C:34]([F:39])([F:38])[C@@H:35]([NH2:37])[CH3:36].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:29]([NH:37][C@@H:35]([CH3:36])[C:34]([F:39])([F:38])[F:33])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][C:18]=2[F:32])=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10964447(S)-1,1,1-trifluoropropan-2-amineHCID 903144344'-(2-Aminopyrimidin-5-yl)-3'-fluoro-[1,1'-biphenyl]-2-carboxylic acid

Product 1

HCID 903137394'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]biphenyl-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of DIPEA (47 mg, 0.36 mmol) in DMF (2 mL) were added 4′-(2-aminopyrimidin-5-yl)-3′-fluoro-[1,1′-biphenyl]-2-carboxylic acid (75 mg, 0.24 mmol), (S)-1,1,1-trifluoropropan-2-amine (30 mg, 0.27 mmol) and HATU (110 mg, 0.290 mmol).

Sources & evidence

ORD record
ord-29ab8604de1e40ddb468dbd3916da303
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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