3-(6,7-Dimethoxyquinazolin-4-ylthio)aniline → US9730937, Example 347

HRID 631701Notes

Reaction equation

HRID 631701 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([CH3:51])[CH:28]=[CH:27][C:26]([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: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:26]3[CH:25]=[CH:24][C:23]([CH3:51])=[CH:28][CH:27]=3)[N:30]=[C:31]([C:44]3([C:47]([F:50])([F:49])[F:48])[CH2:45][CH2:46]3)[CH:32]=2)=[O:36])[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 569536273-(6,7-Dimethoxyquinazolin-4-ylthio)anilineHCID 66876638phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate

Product 1

HCID 44243081US9730937, Example 347Yield 83.3%

Procedure

The title compound was prepared from 3-(6,7-dimethoxyquinazolin-4-ylthio)aniline (94 mg, 0.3 mmol) and the carbamate from Example 346A (120 mg, 0.3 mmol) using the procedure in Example 115C to give 1-(3-(6,7-dimethoxyquinazolin-4-ylthio)phenyl)-3-(1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-yl)urea (152 mg, 0.25 mmol, 82%). 1H NMR (300 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.69 (s, 1H), 8.55 (s, 1H), 7.79 (s, 1H), 7.51-7.32 (m, 8H), 7.25 (d, 1H), 6.54 (s, 1H), 3.99 (s, 6H), 2.38 (s, 3H), 1.38-1.27 (m, 4H); LC-MS (ESI) m/z 621 (M+H)+.

Sources & evidence

ORD record
ord-6f1e1d79716c4ac79cf3cb03d6d923de
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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