Phenylacetyl isothiocyanate → N-(4-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide

HRID 500892Notes

Reaction equation

HRID 500892 reaction equation
[NH:1]1[C:5]2=[C:6]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=3[F:18])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[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>[NH:1]1[C:5]2=[C:6]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:29]([NH:28][C:26](=[O:27])[CH2:25][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[S:30])=[CH:13][C:12]=3[F:18])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 594246294-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 58621945N-(4-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 261 (44 mg, 0.18 mmol) and 2-phenylacetyl isothiocyanate (36 □L, 0.19 mmol) in THF (2 mL) was stirred at room temperature for 2 hours, and concentrated. The residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1), to afford the title compound 262a (30 mg, 40%) as an off-white solid. 1H NMR (DMSO-d6) δ (ppm): 12.41(s, 1H), 12.07(s, 1H), 11.77(s, 1H), 7.84(dd, 1H, J=10.95 Hz, J2=2.0 Hz), 7.58(t, 1H), J1=J2=2.7 Hz), 7.51(d, 1H, J=5.7 Hz), 7.43-7.39(m, 2H), 7.37-7.33(m, 4H), 7.31-7.26(m, 2H), 6.55(dd, 1H, J1=1.76 Hz, J2=2.9 Hz), 3.84(s, 2H), MS (m/z): 421.1(M+H) (found).

Workup

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

Sources & evidence

ORD record
ord-7592a01ff07a472e81f8c2b026ad0c05
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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