2-(Trifluoromethyl)benzylamine → HCID 21916466, compound

HRID 1246242Notes

Reaction equation

HRID 1246242 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20](O)=[O:21])[CH:12]=2)=[CH:6][CH:5]=1.[F:28][C:29]([F:39])([F:38])[C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO.ClCCl>[F:27][C:2]([F:1])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:33][CH2:32][C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[C:29]([F:38])([F:39])[F:28])=[O:21])[CH:12]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 764472-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 5311512HCID 5311512, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 21916466HCID 21916466, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 3-[6-(4-trifluoromethoxy-phenylamino)-pyrimidin-4-yl]-benzoic acid (100 mg, 0.27 mmol), 2-trifluoromethylbenzyl amine (71 mg, 0.40 mmol), HATU (112 mg, 0.30 mmol) and DIPEA (232 μL, 1.33 mmol) in DMF (4 mL) is stirred at room temperature for eight hours. The solvent is then removed and silica gel chromatography (methanol/dichloromethane, 5/95) affords the title compound, 3-[6-(4-Trifluoromethoxy-phenylamino)-pyrimidin-4-yl]-N-(2-trifluoromethyl-benzyl)-benzamide (134 mg, 95% yield); 1H NMR (400 MHz, d-DMSO) δ4.71 (d, J=5.1 Hz, 2H), 7.36 (m, 3H), 7.49 (m, 1H), 7.56 (d, J=7.5 Hz, 1H), 7.67 (m, 2H), 7.75 (d, J=7.9 Hz, 1H), 7.85 (d, J=9.1 Hz, 2H), 8.08 (d, J=7.8 Hz, 1H), 8.23 (d, J=7.7 Hz, 1H), 8.61 (s, 1H), 8.78 (s, 1H), 9.31 (dd, J=5.8, 6.0 Hz, 1H), 9.96 (s, 1H); MS (ES+) m/e 533.1(M+H+).

Workup

  1. customThe solvent is then removed

Sources & evidence

ORD record
ord-834964274b1744e4a6c88273fa0e0cca
Source dataset
uspto-grants-2006_10
Patent number
US07125997B2

Reaction notes

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