Diethyl Ether → HCID 58267792, compound

HRID 1918003Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][N:7]=[C:6]2[S:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].[CH:26]([C:29]1[O:33][N:32]=[C:31]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)[CH:30]=1)([CH3:28])[CH3:27].[CH2:44](OCC)[CH3:45]>>[CH:26]1([C:29]2[O:33][N:32]=[C:31]([NH:34][C:35]([NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:19]([S:18][C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=[CH:8][N:7]=4)[CH:20]=3)=[O:43])[CH:30]=2)[CH2:27][CH2:45][CH2:44][CH2:28]1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 59394199HCID 59394199, compound

HCID 668767643-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)aniline

Product 1

HCID 58267792HCID 58267792, compoundYield 53%

Procedure

Using the procedure described in Example 113C compound 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)aniline described in Example 231A (114 mg, 0.32 mmol) was reacted with phenyl 5-isopropylisoxazol-3-ylcarbamate described in Example 135A (130 mg, 0.48 mmol). Upon addition of dietyl ether, the solid was filtered off and washed with diethyl ether to give 1-(5-cyclopentylisoxazol-3-yl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)phenyl)urea (91.12 mg, 53%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.52 (s, 1H), 9.07 (s, 1H), 8.68 (s, 1H), 7.79 (s, 1H), 7.59-7.41 (m, 2H), 7.41-7.24 (m, 3H), 6.50 (s, 1H), 4.39-4.24 (m, 2H), 4.00 (s, 3H), 3.88-3.66 (m, 2H), 3.34 (s, 3H), 3.25-3.04 (m, 1H), 2.09-1.88 (m, 2H), 1.75-1.48 (m, 6H); LC-MS (ESI) m/z 536 (M+H)+.

Workup

filtrationthe solid was filtered off
washwashed with diethyl ether

Sources & evidence

ORD record: ord-ba5a5839ab23401289f0463e1df9cdc7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618289B2

Reaction notes

Loading…