4-(Chloromethyl)-1,3-thiazole hydrochloride → HCID 57974318, compound

HRID 1864249Notes

Reaction equation

HRID 1864249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][C@H:21]([CH3:28])[CH2:22][N:23]([CH3:27])[C:24](=[O:26])[CH3:25])[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl.Cl[CH2:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][C@H:21]([CH3:28])[CH2:22][N:23]([CH3:27])[C:24](=[O:26])[CH3:25])[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1

Participants

3

Reactant 2

HCID 27632894-(Chloromethyl)-1,3-thiazole hydrochlorideHCID 69059499HCID 69059499, compound

Product 1

HCID 57974318HCID 57974318, compoundYield 17%

Procedure

The procedure described in Example 3 was repeated using N-[(2R)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)propyl]-N-methylacetamide (obtained as described for in Example 50, preparation of starting materials) and 4-(chloromethyl)-thiazole hydrochloride to give the title compound in 17% yield; NMR spectrum (DMSO-d6) 1.36 (d, 3H), 1.94 (s, 3H), 3.02 (s, 3H), 3.3O (1H obscured by H2O), 4.21 (dd, 1H), 5.09 (m, 1H), 5.33 (s, 2H), 7.29 (m, 3H), 7.70 (m, 2H), 7.81 (s, 1H), 8.08 (s, 1H), 8.47 (s, 1H), 9.13 (s, 1H), 9.96 (s, 1H); Mass Spectrum MH+ 498.

Sources & evidence

ORD record
ord-3a5cdfb4d80a44fa81bde7efb52c4c7d
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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