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

HRID 1261304Notes

Reaction equation

HRID 1261304 reaction equation
[CH3:1][S:2]([C:4]1[S:12][C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[F:21])[CH:5]=1)=[O:3].[C:22]1([CH2:28][C:29]([N:31]=[C:32]=[S:33])=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH3:1][S:2]([C:4]1[S:12][C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:32]([NH:31][C:29](=[O:30])[CH2:28][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[S:33])=[CH:16][C:15]=2[F:21])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 594245284-(2-(Methylsulfinyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 594245741-(4-(2-(Methylsulfinyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thioureaYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 234 (280 mg, 0.868 mmol) in THF (8 mL) was added 2-phenyl acetyl isothiocyanate (185 mg, 1.04 mmol). The reaction mixture was stirred for 3 hours, concentrated; the solid residue washed with Et2O and dried, to afford title compound 235 (229 mg, 53% yield) as a white-rose solid. 1HNMR: (DMSO-d6) δ (ppm): 12.41(s, 1H), 11.75(s, 1H), 8.54(d, J=5.3 Hz, 1H), 7.98 (s, 1H), 7.96(d, J=13.5 Hz, 1H), 7.48(d, J=5.0 Hz, 2H), 7.30-7.26(m, 2H), 7.26-7.18(m, 3H), 6.69(d, J=5.5 Hz, 1H), 3.25(s, 2H), 2.98(s, 3H). MS (m/z): 500.1 (M+1).

Workup

  1. concentrationconcentrated
  2. washthe solid residue washed with Et2O
  3. customdried

Sources & evidence

ORD record
ord-9cbd8eb6497d476e91503465f7ec3375
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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