4-(Chloromethyl)-1,3-thiazole hydrochloride → HCID 69062105, compound

HRID 1864283Notes

Reaction equation

HRID 1864283 reaction equation
[NH2:1][CH2:2][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[CH2:26][C:27]1[N:28]=[CH:29][S:30][CH:31]=1>>[NH2:1][CH2:2][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][CH2:26][C:27]3[N:28]=[CH:29][S:30][CH:31]=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 69063573HCID 69063573, compound

Product 1

HCID 69062105HCID 69062105, compoundYield 91%

Procedure

The procedure described in Example 65 (preparation of starting materials) was repeated using 4-{[5-(2-aminoethoxy)quinazolin-4-yl]amino}-2-chlorophenol and 4-(chloromethyl)-1,3-thiazole hydrochloride to give 5-(2-aminoethoxy)-N-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)phenyl]quinazolin-4-amine in 91% yield; NMR spectrum (DMSO-d6 400 MHz) 3.02-3.19 (bs, 2H), 4.22-4.36 (m, 2H), 5.33 (s, 2H), 7.14 (d, 1H), 7.27-7.40 (m, 2H), 7.67-7.86 (m, 3H), 8.23 (s, 1H), 8.52 (s, 1H), 9.15 (s, 1H) (3 exchangeables); Mass spectrum MH+ 427.9.

Workup

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

Sources & evidence

ORD record
ord-9f058b3e91cf45bbbf74cb601a28b450
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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