3-(Trifluoromethyl)aniline → 3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamide

HRID 883917Notes

Reaction equation

HRID 883917 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:17](Cl)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:32]=1)([CH3:3])[CH3:2].[F:33][C:34]([F:43])([F:42])[C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38].NC1C=C(O)C(C)=CC=1>CO>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:17]([NH:38][C:37]3[CH:39]=[CH:40][CH:41]=[C:35]([C:34]([F:33])([F:42])[F:43])[CH:36]=3)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:32]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 178185-Amino-2-methylphenolHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

Product 1

HCID 247576143-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 14B was reacted with 3-(trifluoromethyl)aniline according to the procedure from Example 14C substituting 3-(trifluoromethyl)aniline for 5-amino-o-cresol to provide the title compound as an off white solid after trituration of the reaction product from methanol (73 mg, 77%). 1 H NMR (300 MHz, DMSO-D6) δ ppm: 10.54 (s, 1 H), 8.93 (d, J=8.46 Hz, 1 H), 8.67 (s, 1 H), 8.22 (s, 1 H), 8.04 (d, J=8.09 Hz, 1 H), 7.99 (s, 1 H), 7.85 (d, J=7.72 Hz, 1 H), 7.74 (d, J=8.46 Hz, 1 H), 7.59 (t, J=8.09 Hz, 1 H), 7.45 (d, J=8.46 Hz, 1 H), 7.41 (d, J=8.82 Hz, 2 H), 6.92-7.11 (m, 4 H), 3.77 (s, 3 H), 3.20-3.31 (m, 1 H), 1.35 (d, J=6.62 Hz, 6 H); MS (ESI+) m/z 590.3 (M+H)+, (ESI−) m/z 588.1 (M−H)−.

Sources & evidence

ORD record
ord-a52604b638014d0eb36023ee0ca7aebe
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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