4-(Chloromethyl)-1,3-thiazole → HCID 57974346, compound

HRID 1864319Notes

Reaction equation

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

Participants

Reactant 2

HCID 27632904-(Chloromethyl)-1,3-thiazole

HCID 69061256HCID 69061256, compound

Product 1

HCID 57974346HCID 57974346, compoundYield 13%

Procedure

The procedure described in Example 3 was repeated using 4-(chloromethyl)-1,3-thiazole and N-[(1R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-N-methylacetamide (obtained as described in Example 93, preparation of starting materials) to give the title compound as a white solid in 13% yield; NMR spectrum (DMSO-d6 373K) 1.22 (d, 3H), 1.86 (s, 3H), 2.24 (s, 3H), 2.85 (s, 3H), 4.33 (m, 1H), 4.42 (t, 1H), 5.09 (m, 1H), 5.25 (s, 2H), 7.09 (d, 1H), 7.18 (d, 1H), 7.34 (d, 1H), 7.39 (s, 1H), 7.50 (d, 1H), 7.70 (m, 2H), 8.41 (s, 1H), 9.08 (s, 1H), 9.51 (s, 1H); Mass spectrum MH+ 478.

Sources & evidence

ORD record: ord-110e013a6c324067acb16bbd76161b82
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

Loading…