N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide → 1-(3-Aminophenyl)-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}methanesulfonamide

HRID 541830Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([NH:15][S:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:29])=[CH:4][N:3]=1>O.CO.C(O)(=O)C.[Fe]>[NH2:26][C:22]1[CH:21]=[C:20]([CH2:19][S:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]3[C:5]([Cl:29])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:10]=2)(=[O:17])=[O:18])[CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide (0.060 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. Water phase was extracted with EtOAc twice. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a yellow powder (0.050 g, 89%. LCMS for C17H15Cl2N5O2S (M+H)+: m/z=423.9, 426.0.

Workup

additionThe reaction was mixed with celite
filtrationfiltered
washthe cake was washed with EtOAc
concentrationThe brown filtrate was concentrated
additionEtOAc and NaHCO3/water added
extractionWater phase was extracted with EtOAc twice
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-be994e1bf78f4e3ca20b4602eb0b597f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

Loading…