3-(6,7-Dimethoxyquinazolin-4-ylthio)aniline → 3-(1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-yl)urea

HRID 631748Notes

Reaction equation

HRID 631748 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[S:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].[C:23]1([N:29]2[C:33]([NH:34][C:35](=O)[O:36]C3C=CC=CC=3)=[CH:32][C:31]([C:44]3([C:47]([F:50])([F:49])[F:48])[CH2:46][CH2:45]3)=[N:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[S:15][C:16]1[CH:17]=[C:18]([NH:19][C:35]([NH:34][C:33]2[N:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:30]=[C:31]([C:44]3([C:47]([F:50])([F:48])[F:49])[CH2:46][CH2:45]3)[CH:32]=2)=[O:36])[CH:20]=[CH:21][CH:22]=1.[C:23]1([N:29]2[C:33]([NH:34][C:35](=[O:36])[NH2:7])=[CH:32][C:31]([C:44]3([C:47]([F:49])([F:50])[F:48])[CH2:46][CH2:45]3)=[N:30]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 569536273-(6,7-Dimethoxyquinazolin-4-ylthio)anilineHCID 67159116phenyl 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate

Product 2

HCID 58267725US9730937, Example 383HCID 1317354233-(1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-yl)ureaYield 173.3%

Procedure

The title compound was prepared from 3-(6,7-dimethoxyquinazolin-4-ylthio)aniline (94 mg, 0.3 mmol) and the carbamate from Example 137A (116 mg, 0.3 mmol) using the procedure in Example 115C to give 14346,7-dimethoxyquinazolin-4-ylthio)phenyl)-3-(1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-yl)urea (160 mg, 0.26 mmol, 88%). 1H NMR (300 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.69 (s, 1H), 8.61 (s, 1H), 7.79 (s, 1H), 7.58-7.50 (m, 4H), 7.49-7.38 (m, 3H), 7.34 (d, 2H), 7.25 (d, 1H), 6.56 (s, 1H), 3.99 (s, 6H), 1.35-1.29 (m, 4H); LC-MS (ESI) m/z 607 (M+H)+.

Sources & evidence

ORD record
ord-cad4294772ad401b8d7e77707d606ddc
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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