1,1-Dimethylethyl (3-{[5-nitro-4-({4-[(phenylmethyl)oxy]phenyl}amino)-2-pyridinyl]oxy}phenyl)carbamate → 1,1-Dimethylethyl [3-({5-amino-4-[(4-hydroxyphenyl)amino]-2-pyridinyl}oxy)phenyl]carbamate

HRID 1986381Notes

Reaction equation

HRID 1986381 reaction equation
[N+:1]([C:4]1[C:5]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32]CC3C=CC=CC=3)=[CH:28][CH:27]=2)=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[CH:15][CH:16]=2)=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:5]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH:14]=[CH:15][CH:16]=2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 866233501,1-Dimethylethyl (3-{[5-nitro-4-({4-[(phenylmethyl)oxy]phenyl}amino)-2-pyridinyl]oxy}phenyl)carbamate

Product 1

HCID 866233511,1-Dimethylethyl [3-({5-amino-4-[(4-hydroxyphenyl)amino]-2-pyridinyl}oxy)phenyl]carbamateYield 102.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product from Step 2 (16.4 g, 31.0 mmol) was hydrogenated with a balloon of H2 in the presence of 5% Pd/C (2 g) in MeOH (100 mL) over the weekend. The reaction mixture was then filtered through Celite and concentrated to give the title compound (13 g, quant.) which was used without purification. MS (ES+) m/e 409 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a01e1b158c3e4d179214d6e6e075abc7
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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