4-(Chloromethyl)-1,3-thiazole hydrochloride → HCID 69058325, compound

HRID 1864287Notes

Reaction equation

HRID 1864287 reaction equation
[NH2:1][C@H:2]([CH3:24])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([Cl:23])[CH:17]=1)=[N:8][CH:9]=[N:10]2.Cl.Cl[CH2:27][C:28]1[N:29]=[CH:30][S:31][CH:32]=1>>[NH2:1][C@H:2]([CH3:24])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:27][C:28]3[N:29]=[CH:30][S:31][CH:32]=3)=[C:18]([Cl:23])[CH:17]=1)=[N:8][CH:9]=[N:10]2

Participants

3

Reactant 2

HCID 27632894-(Chloromethyl)-1,3-thiazole hydrochlorideHCID 69061093HCID 69061093, compound

Product 1

HCID 69058325HCID 69058325, compoundYield 65%

Procedure

The procedure described in Example 65 (preparation of starting materials) was repeated using 4-[(5-{[(2R)-2-aminopropyl]oxy}quinazolin-4-yl)amino]-2-chlorophenol and 4-(chloromethyl)-1,3-thiazole hydrochloride give 5-{[(2R)-2-aminopropyl]oxy}-N-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)phenyl]quinazolin-4-amine in 65% yield; NMR spectrum (DMSO-d6) 1.17 (d, 3H), 3.33-3.45 (m, 1H), 4.00 (dd, 1H)), 4.24 (dd, 1H), 5.32 (s, 2H), 7.11 (d, 1H), 7.30 (d, 1H), 7.33 (d, 1H), 7.67-7.82 (m, 3H), 8.23 (d, 1H), 8.51 (s, 1H), 9.14 (d, 1H); Mass spectrum MH+ 441.9.

Workup

  1. customThe procedure described in Example 65 (preparation of starting materials)

Sources & evidence

ORD record
ord-e95ee0cc02154373987c9b98a40c5dc6
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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