2-(Chloromethyl)-1,3-thiazole → HCID 57974282, compound

HRID 1864305Notes

Reaction equation

Cl[CH2:2][C:3]1[S:4][CH:5]=[CH:6][N: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[S:4][CH:5]=[CH:6][N:7]=3)=[C:30]([CH3:35])[CH:29]=1)=[N:20][CH:21]=[N:22]2)[CH3:15])=[O:11]

Participants

Reactant 2

HCID 140908642-(Chloromethyl)-1,3-thiazole

HCID 69056760HCID 69056760, compound

Product 1

HCID 57974282HCID 57974282, compoundYield 31%

Procedure

The procedure described in Example 3 was repeated using 2-(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 light brown solid in 31% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.25 (s, 3H), 3.42 (dt, 1H), 3.73 (m, 1H), 3.79 (d, 2H), 4.94 (m, 1H), 5.44 (s, 2H), 5.47 (t, 1H), 7.09 (d, 1H), 7.23 (d, 1H), 7.30 (d, 1H), 7.58 (d, 1H), 7.63 (dd, 1H), 7.69 (t, 1H), 7.77 (d, 1H), 7.84 (d, 1H), 8.16 (t, 1H), 8.43 (s, 1H), 9.96 (s, 1H); Mass spectrum MH+ 480.

Sources & evidence

ORD record: ord-7d87caf7e0a04fa986f21712fafefaac
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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