Phenylacetyl isothiocyanate → N-(3-Fluoro-4-(6-(methylthio)thieno[3,2-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamide

HRID 500905Notes

Reaction equation

HRID 500905 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[S:17][C:16]([S:18][CH3:19])=[CH:15][C:11]=2[N:12]=[CH:13][N:14]=1.[C:21]1([CH2:27][C:28]([N:30]=[C:31]=[S:32])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:20][C:31]([NH:30][C:28](=[O:29])[CH2:27][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[S:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[S:17][C:16]([S:18][CH3:19])=[CH:15][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 594245863-Fluoro-4-(6-(methylthio)thieno[3,2-d]pyrimidin-4-yloxy)benzenamine

Product 1

HCID 59424579N-(3-Fluoro-4-(6-(methylthio)thieno[3,2-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamideYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 282 (248mg, 0.80 mmol) and 2-phenylacetyl isothiocyanate (214 mg, 1.20 mmol) in THF (8 mL) was stirred for 2 hours, and concentrated. The residue was purified by flash column chromatography, eluent EtOAc/hexane (3:7), to afford title compound 283 (200 mg, 52% yield) as an off-white solid. 1H NMR (DMSO-d6) δ (ppm): 12.42(s, 1H), 11.80(s, 1H), 8.63(s, 1H), 7.85(d, 1H), 7.54-7.44 (m, 3H), 7.35 (m, 4H), 7.30(m, 1H), 3.81(s, 2H), MS (m/z): 485.1 (M+H) (found).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography, eluent EtOAc/hexane (3:7)

Sources & evidence

ORD record
ord-0aa9055bf2a748c794b9daf0429b8539
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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