Ethanol → HCID 86700429, compound
Reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].O1[CH2:40][CH2:39]OCC1.O.[OH-].[Na+].[CH2:44](O)[CH3:45]>>[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:15]4[CH2:45][CH2:44][N:19]([CH2:39][CH3:40])[CH2:18][CH2:16]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]Participants
6
Conditions
- Temperature
- 90 °C
Procedure
(S)-Methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (10 mg), dioxane (500 μL), and H2O (200 μL) were added. The reaction was heated to 90° C. for 1 h. Ethanol (absolute, 500 μL) and 5 M aq NaOH (500 μL) were added and the reaction was heated to 90° C. for 30 min. The reaction was cooled to 23° C. and directly purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) giving the title compound. 1H NMR (400 MHz, CD3OD) δ 8.62 (d, J=5.0 Hz, 1H), 7.91 (s, 1H), 7.74-7.49 (m, 5H), 5.24 (s, 1H), 3.37-3.28 (m, 8H), 3.24 (q, J=7.4 Hz, 2H), 2.62 (s, 3H), 1.38 (t, J=7.3 Hz, 2H), 0.97 (s, 9H). LCMS-ESI+: calc'd for C30H35ClN5O3S [M+H+]: 580.2, 582.2; Found: 580.4, 582.2 (M+H+).
Workup
- temperaturethe reaction was heated to 90° C. for 30 min
- temperatureThe reaction was cooled to 23° C.
- customdirectly purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA)
Sources & evidence
- ORD record
- ord-33964e752a1b4adca2da49d84948d1a1
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987250B2
Reaction notes
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