4-(Chloromethyl)-1,3-thiazole → HCID 57974293, compound

HRID 1864308Notes

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

Participants

Reactant 2

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

HCID 69060818HCID 69060818, compound

Product 1

HCID 57974293HCID 57974293, compoundYield 20%

Procedure

The procedure described in Example 3 was repeated using 4-(chloromethyl)-1,3-thiazole and N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide (obtained as described in Example 86, preparation of starting materials) to give the title compound as a white solid in 20% yield; NMR spectrum (DMSO-d6) 1.41 (d, 3H), 1.78 (s, 3H), 2.23 (s, 3H), 3.41 (dt, 1H), 3.58 (dt, 1H), 4.87 (m, 1H), 5.25 (s, 2H), 7.11 (d, 1H), 7.21 (d, 1H), 7.29 (d, 1H), 7.53 (d, 1H), 7.63 (dd, 1H), 7.69 (t, 1H), 7.76 (d, 1H), 8.23 (t, 1H), 8.44 (s, 1H), 9.14 (d, 1H), 9.96 (s, 1H); Mass spectrum MH+ 464.

Sources & evidence

ORD record: ord-8d62b453da2549be92a6019f285d4303
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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