Phenylacetyl isothiocyanate → N-(3-Fluoro-4-(2-(4-(methylsulfonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide

HRID 1710910Notes

Reaction equation

HRID 1710910 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[S:17][C:10]=12.[C:29]1([CH2:35][C:36]([N:38]=[C:39]=[S:40])=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:28][C:39]([NH:38][C:36](=[O:37])[CH2:35][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[S:40])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:22][CH:23]=3)[S:17][C:10]=12

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 587728693-Fluoro-4-(2-(4-(methylsulfonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Product 1

HCID 58772875N-(3-Fluoro-4-(2-(4-(methylsulfonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 49 (46.7 mg, 0.1 mmol) in dry THF (5 mL), 2-phenylacetyl isothiocyanate (40 mg, 0.2 mmol) was added and the reaction was allowed to stir for 30 minutes. The THF was removed under reduced pressure and the resultant product was purified by column chromatography on silica gel, eluent hexane/EtOAc (1:1), to afford the title compound 50 (35.4 mg, 53% yield). 1HNMR (DMSO) δ (ppm): 12.49 (s, 1H), 11.85 (s, 1H), 8.57 (d, J=5.5 Hz, 1H), 8.30 (s, 1H), 8.17 (d, J=8.4 Hz, 2H), 8.02 (d, J=8.4 Hz, 2H), 7.63-7.52 (m, 5H), 7.34 (d, J=4.1 Hz, 2H), 6.71 (d, J=5.3 Hz, 1H), 3.82 (brs, 2H), 3.27 (s, 3H) MS (m/z) 592.0 (M+).

Workup

  1. customThe THF was removed under reduced pressure
  2. customthe resultant product was purified by column chromatography on silica gel, eluent hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-02a389bf6fcb4c95a7b3028b01ebe775
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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