N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-2-(3-nitrophenyl)acetamide → 2-(3-Aminophenyl)-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}acetamide

HRID 541834Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:27])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:28])=[CH:4][N:3]=1>O.CO.C(O)(=O)C.[Fe]>[NH2:24][C:20]1[CH:19]=[C:18]([CH2:17][C:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]3[C:5]([Cl:28])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:10]=2)=[O:27])[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}-2-(3-nitrophenyl)acetamide (0.055 g, 0.13 mmol) in water (0.1 mL), methanol (0.5 mL) and acetic acid (0.20 mL) was added iron (0.030 g, 0.53 mmol) powder in one batch. The mixture was stirred at 0° C. for 0.5 h. The reaction was mixed with celite, filtered, and the cake was washed with EtOAc. The brown filtrate was concentrated and EtOAc and NaHCO3/water added. The aqueous phase was extracted with EtOAc. The organics were combined, died over Na2SO4 and concentrated to give the desired product as a yellow powder (30 mg, 58%). LCMS for C18H15Cl2N5O (M+H)+: m/z=388.0, 390.0.

Workup

additionThe reaction was mixed with celite
filtrationfiltered
washthe cake was washed with EtOAc
concentrationThe brown filtrate was concentrated
additionEtOAc and NaHCO3/water added
extractionThe aqueous phase was extracted with EtOAc
concentrationconcentrated

Sources & evidence

ORD record: ord-3e28a96499b745ad87d64d96c093d0fc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

Loading…