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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 541834
Notes
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Reaction equation

HRID 541834 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 57962398N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-2-(3-nitrophenyl)acetamide

Product 1

HCID 579627352-(3-Aminophenyl)-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}acetamideYield 59.4%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887Methanol
Solvent
HCID 962WaterSolvent

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

  1. additionThe reaction was mixed with celite
  2. filtrationfiltered
  3. washthe cake was washed with EtOAc
  4. concentrationThe brown filtrate was concentrated
  5. additionEtOAc and NaHCO3/water added
  6. extractionThe aqueous phase was extracted with EtOAc
  7. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes