N,O-Dimethylhydroxylamine → HCID 86624858, compound

HRID 1697106Notes

Reaction equation

HRID 1697106 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]3[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]3[CH3:24])[N:13]=2)[CH:3]=1.[CH3:25][O:26][NH:27][CH3:28]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:27]([O:26][CH3:25])[CH3:28])=[O:8])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]3[C:19]([CH3:24])=[CH:20][CH:21]=[C:22]3[CH3:23])[N:13]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 66816010HCID 66816010, compound

Product 1

HCID 86624858HCID 86624858, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-benzoic acid (4.2 g) in DMF (25 mL) and carbonyldiimide (2.4 g) was stirred at 60° C. for 30 min, and N-methoxy-N-methylamine (1.41 g) was added. The mixture was stirred at 80° C. for 16 h, then the volatiles evaporated, and the residue partitioned between EtOAc and H2O, then between EtOAc and HCl (0.1 N aq). The organic phase was adsorbed on silica gel and chromatographed. Chromatography on silica (80 g) against hexane/EtOAc (100:0 to 50:50) provided 4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-N-methoxy-N-methyl-benzamide (˜1.6 g).

Workup

  1. stirringThe mixture was stirred at 80° C. for 16 h
  2. customthe volatiles evaporated
  3. customthe residue partitioned between EtOAc and H2O
  4. customchromatographed

Sources & evidence

ORD record
ord-866b557661bb4854818ea1d85ae4291e
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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