Phenylacetyl isothiocyanate → 1-(4-(2-(Methylsulfonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

HRID 1711012Notes

Reaction equation

HRID 1711012 reaction equation
[CH3:1][S:2]([C:5]1[S:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[F:22])[CH:6]=1)(=[O:4])=[O:3].[C:23]1([CH2:29][C:30]([N:32]=[C:33]=[S:34])=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.CO>[CH3:1][S:2]([C:5]1[S:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:33]([NH:32][C:30](=[O:31])[CH2:29][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[S:34])=[CH:17][C:16]=2[F:22])[CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 594245404-(2-(Methylsulfonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 594245901-(4-(2-(Methylsulfonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thioureaYield 31.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 237 (20 mg, 0.059 mmol) in THF (10 mL) was added 2-phenylacetyl isothiocyanate (26 mg, 0.146 mmol). The reaction mixture was stirred for 2 hours, concentrated under reduced pressure and the residue was purified by column chromatography, eluent EtOAc/MeOH (19:1), to afford a solid material that was dissolved in a minimum MeOH and precipitated with hexane to afford title compound 238 (9.6 mg, 31%) as a white solid. 1HNMR: (DMSO-d6) δ (ppm): 12.48 (s, 1H), 11.81 (s, 1H), 8.69(d, J=5.5 Hz, 1H), 8.36 (s, 1H), 8.03(d, J=12.13 Hz, 1H), 7.55 (s, 2H), 7.36-7.30 (m, 2H), 7.30-7.24 (m, 3H), 6.86(d, J=5.5 Hz, 1H), 3.83 (s, 2H), 3.54 (s, 3H). MS (m/z): 516.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by column chromatography, eluent EtOAc/MeOH (19:1)
  3. customto afford a solid material that
  4. customprecipitated with hexane

Sources & evidence

ORD record
ord-dd6b864e4a1d47279d7fd17730c02238
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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