4-(Chloromethyl)-1,3-thiazole → HCID 57974304, compound

HRID 1864320Notes

Reaction equation

HRID 1864320 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH2:28][C@H:29]([N:31]([CH3:36])[C:32](=[O:35])[CH2:33][OH:34])[CH3:30])[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[OH:15]>>[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH2:28][C@H:29]([N:31]([CH3:36])[C:32](=[O:35])[CH2:33][OH:34])[CH3:30])[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1

Participants

3

Reactant 2

HCID 27632904-(Chloromethyl)-1,3-thiazoleHCID 69055632HCID 69055632, compound

Product 1

HCID 57974304HCID 57974304, compoundYield 64%

Procedure

The procedure described in Example 3 was repeated using 4-(chloromethyl)-1,3-thiazole and N-[(1R)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-2-hydroxy-N-methylacetamide (obtained as described in Example 54, preparation of starting materials) to give the title compound as a white solid in 64% yield; NMR spectrum (DMSO-d6 373K) 1.25 (d, 3H), 2.83 (s, 3H), 3.98 (s, 2H), 4.34 (m, 1H), 4.47 (t, 1H), 4.98 (m, 1H), 5.34 (s, 2H), 7.19 (d, 1H), 7.37 (d, 2H), 7.51 (dd, 1H), 7.70 (t, 1H), 7.74 (d, 1H), 7.93 (d, 1H), 8.46 (s, 1H), 9.08 (s, 1H), 9.57 (s, 1H); Mass spectrum MH+ 514.

Sources & evidence

ORD record
ord-9874b7c5fc3a4304885e3e2e673e479d
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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