Phenyl 3-tert-butylisoxazol-5-ylcarbamate → 1-(3-(6,7-Bis(2-methoxyethoxy)quinazolin-4-ylthio)phenyl)-3-(3-tert-butylisoxazol-5-yl)urea

HRID 871611Notes

Reaction equation

HRID 871611 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[S:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].[C:29]([C:33]1[CH:37]=[C:36]([NH:38][C:39](=O)[O:40]C2C=CC=CC=2)[O:35][N:34]=1)([CH3:32])([CH3:31])[CH3:30]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[S:21][C:22]1[CH:23]=[C:24]([NH:25][C:39]([NH:38][C:36]2[O:35][N:34]=[C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:37]=2)=[O:40])[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 59394466Phenyl 3-tert-butylisoxazol-5-ylcarbamateHCID 668768743-(6,7-Bis(2-methoxyethoxy)quinazolin-4-ylthio)aniline

Product 1

HCID 582677711-(3-(6,7-Bis(2-methoxyethoxy)quinazolin-4-ylthio)phenyl)-3-(3-tert-butylisoxazol-5-yl)ureaYield 52%

Procedure

The title compound was prepared as described in Example 113C by using compound 3-(6,7-bis(2-methoxyethoxy)quinazolin-4-ylthio)aniline (138 mg, 0.34 mmol) and phenyl 3-tert-butylisoxazol-5-ylcarbamate described in Example 132A (116 mg, 0.45 mmol) to give 1-(3-(6,7-bis(2-methoxyethoxy)quinazolin-4-ylthio)phenyl)-3-(3-tert-butylisoxazol-5-yl)urea (100 mg, 52%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.20 (s, 1H), 9.05 (s, 1H), 8.69 (s, 1H), 7.85 (s, 1H), 7.46 (d, 1H), 7.45-7.38 (m, 3H), 7.31 (d, 1H), 6.05 (s, 1H), 4.36-4.32 (m, 4H), 3.79-3.76 (m, 4H), 3.37 (s, 6H), 1.24 (s, 9H); LC-MS (ESI) m/z 568 (M+H)+.

Sources & evidence

ORD record
ord-1686c18e6ceb44848ba3f4050b33e0cd
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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