1-(3-Fluoro-4-(3-nitropyridin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea → 1-(4-(3-Aminopyridin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea

HRID 1670282Notes

Reaction equation

HRID 1670282 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19]([NH:21][C:22](=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[O:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-])=O>CO.C1COCC1>[NH2:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([NH:18][C:19]([NH:21][C:22](=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[O:20])=[CH:3][C:2]=1[F:1]

Participants

3

Reactant 1

HCID 598530011-(3-Fluoro-4-(3-nitropyridin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea

Product 1

HCID 115095171-(4-(3-Aminopyridin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)ureaYield 74%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A suspension of 1-(3-fluoro-4-(3-nitropyridin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea (125 mg, 0.29 mmol) in 3:1 MeOH/THF (20 mL) was hydrogenated over Pt2O (50 mg) using H2 from a latex balloon for 6 h. The catalyst was filtered off with the aid of Celite® and the filtrate concentrated to give the title compound (85 mg, 74%) as a white solid. 1H NMR (DMSO-d6) δ 11.03 (s, 1H), 10.55 (s, 1H), 8.03 (s, 1H), 7.75 (dd, 1H, J=2.5, 13.2 Hz), 7.65 (d, 1H, J=5.1 Hz), 7.38-7.35 (m, 3H), 7.23-7.16 (m, 3H), 6.42 (d, 1H, J=5.1 Hz), 5.26 (s, 2H), 3.75 (s, 2H); MS (ESI+): m/z 399.35 (M+H)+.

Workup

  1. customfor 6 h
  2. filtrationThe catalyst was filtered off with the aid of Celite®
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-307bab69aa0f4586aa2d72f6dc94c43c
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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