4-Amino-2-chlorobenzonitrile → 3-(3-Chloro-4-cyanophenylamino)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

HRID 133763

Reaction equation

HRID 133763 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([NH:21][C:22]([C:24]2([CH3:27])[CH2:26][O:25]2)=[O:23])[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19]>>[Cl:10][C:4]1[CH:3]=[C:2]([NH:1][CH2:27][C:24]([OH:25])([CH3:26])[C:22]([NH:21][C:14]2[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:12]([CH3:11])[CH:13]=2)=[O:23])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

3

Reactant 2

HCID 887284-Amino-2-chlorobenzonitrileHCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Product 1

HCID 675265433-(3-Chloro-4-cyanophenylamino)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Procedure

3-(3-Chloro-4-cyanophenylamino)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide was prepared as described in Example 52 starting from 4-amino-2-chlorobenzonitrile and 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-3% methanol). 1H NMR (400 MHz, DMSO-d6): 1.40 (3H, s), 2.52 (3H, s), 3.27 (1H, dd, J=13.8 Hz, J=5.5 Hz), 3.55 (1H, dd, J=13.8 Hz, J=6.9 Hz), 6.12 (1H, s), 6.72 (1H, dd, J=8.8 Hz, J=2.2 Hz), 6.90 (1H, d, J=2.2 Hz), 6.95-6.98 (1H, m), 7.46 (1H, d, J=8.7 Hz), 7.80 (1H, dd, J=8.9 Hz, J=2.3 Hz), 7.83 (1H, d, J=2.0 Hz), 8.02 (1H, d, J=8.9 Hz), 10.05 (1H, s).

Workup

  1. customThe crude product was purified by flash chromatography (dichloromethane-3% methanol)

Sources & evidence

ORD record
ord-1f71bd822ec74e30993542ccd0d0ab3b
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Linked notes

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