4-(Chloromethyl)-1,3-thiazole → HCID 57974286, compound

HRID 1864303Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 69056760HCID 69056760, compound

Product 1

HCID 57974286HCID 57974286, compoundYield 13%

Procedure

The procedure described in Example 3 was repeated using 4-(chloromethyl)-1,3-thiazole and 2-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide (obtained as described in Example 82, preparation of starting materials) to give the title compound as a white solid in 13% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.21 (s, 3H), 3.42 (dt, 1H), 3.71 (dt, 1H), 3.79 (d, 2H), 4.95 (m, 1H), 5.24 (s, 2H), 5.48 (t, 1H), 7.09 (d, 1H), 7.23 (d, 1H), 7.29 (d, 1H), 7.54 (d, 1H), 7.62 (dd, 1H), 7.68 (t, 1H), 7.77 (d, 1H), 8.16 (t, 1H), 8.44 (s, 1H), 9.14 (d, 1H), 9.95 (s, 1H); Mass spectrum MH+ 480.

Sources & evidence

ORD record: ord-47b31786de944eaf9433e0a67713aaa0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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