Phenylacetyl isothiocyanate → N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[CH:17][S:18][C:11]=12)[NH2:5].[C:19]1([CH2:25][C:26]([N:28]=[C:29]=[S:30])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:29]([NH:28][C:26](=[O:27])[CH2:25][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[S:30])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[CH:17][S:18][C:11]=12Participants
Procedure
To a stirred solution of 3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline (0.105 g, 0.403 mmol) in THF (1 mL) was added 2-phenylethanoyl isothiocyanate (0.257 g, 1.45 mmol; prepared according to the procedure described by J. Org. Chem. 1964, 29, 1115-1119). The reaction was stirred for 4 hours at room temperature. The reaction mixture was partially purified by Biotage Flash 40 silica gel chromatography, eluting with a gradient of 10-50% EtOAc in hexanes. The product was further purified by preparative TLC (10% MeOH in CH2Cl2). Yield: 18 mg (9%). 1H NMR (400 MHz, CDCl3) δ 12.55 (s, 1H), 9.00 (s, 1H), 8.53 (d, J=5 Hz, 1H), 7.94 (m, 1H), 7.75 (d, J=5 Hz, 1H), 7.58 (d, J=5 Hz, 1H), 7.08-7.50 (m, 7H), 6.54 (d, J=5 Hz, 1H), 3.75 (s, 2H). LRMS (APCI neg) m/e 436 (M−1).
Workup
- customprepared
- customThe reaction mixture was partially purified by Biotage Flash 40 silica gel chromatography
- washeluting with a gradient of 10-50% EtOAc in hexanes
- customThe product was further purified by preparative TLC (10% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-becde4d1069d44a8954814204cbafdb1
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003662B2
Reaction notes
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