Lithium Hydroxide → 6-{(E)-2-[2-(Isobutoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid
Reaction equation
[OH-].[Li+].[CH:3]1([CH2:6][O:7][C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2/[CH:16]=[CH:17]/[C:18]2[N:19]=[C:20]3[N:24]([C:25]=2[C:26]([OH:28])=[O:27])[CH:23]=[CH:22][S:21]3)[CH2:5][CH2:4]1>>[CH2:6]([O:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:16]=[CH:17]/[C:18]1[N:19]=[C:20]2[N:24]([C:25]=1[C:26]([OH:28])=[O:27])[CH:23]=[CH:22][S:21]2)[CH:3]([CH3:5])[CH3:4]Participants
3
Procedure
Lithium hydroxide assisted hydrolysis of Step 1 intermediate (200 mg, 0.499 mmol) as described in Intermediate 1 gave 170 mg of the desired product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (d, J=6.3 Hz, 6H), 2.14-2.27 (m, 1H), 3.76 (d, J=6.3 Hz, 2H), 3.87 (s, 3H), 6.86 (d, J=7.8 Hz, 1H), 6.95 (d, J=4.5 Hz, 1H), 7.06 (t, J=7.8 Hz, 1H), 7.32 (d, J=7.2 Hz, 1H), 7.84 (d, J=16.2 Hz, 1H), 8.07 (d, J=16.2 Hz, 1H), 8.12-8.17 (m, 1H); APCI-MS (m/z) 373.07 (MH)+.
Sources & evidence
- ORD record
- ord-4fd0b8da7bb043cea44724f5d727c013
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318928B2
Reaction notes
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