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

HRID 500895Notes

Reaction equation

HRID 500895 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[F:18])[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:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:29]([NH:28][C:26](=[O:27])[CH2:25][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[S:30])=[CH:13][C:12]=2[F:18])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 594245934-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 59424591N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenyl acetamideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 268 (20 mg, 0.08 mmol) and 2-phenylacetyl isothiocyanate (16 μL, 0.08 mmol) in THF (1 mL) was stirred at room temperature for 2 hours and concentrated. The residue was purified by flash column chromatography (eluent EtOAc) followed by preparative HPLC (column Aqusil C18, gradient elution with 60-95% MeOH in water, 45 min) to afford the title compound 269a (13 mg, 40% yield) as an off-white solid. 1H NMR (CD3OD) δ (ppm): 8.41(s, 1H), 8.16(d. 1H, J=5.6 Hz), 8.02(dd, 1H, J1=2.3 Hz, J2=12.2 Hz), 7.62(d, 1H, J=3.3 Hz), 7.44(m, 1H), 7.37-7.33(m, 4H) 7.31-7.26(m, 1H), 6.65(d, 1H, J=3.1 Hz), 6.52(d, 1H, J=5.7 Hz), 3.76(s, 2H), MS (m/z): 421.1(M+H) (found).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography (eluent EtOAc)
  3. washfollowed by preparative HPLC (column Aqusil C18, gradient elution with 60-95% MeOH in water, 45 min)

Sources & evidence

ORD record
ord-d845aecd6b76470ba1d1082b46dffae4
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

Loading…