O-Methylhydroxylamine hydrochloride → HCID 57378999, compound

HRID 1184384Notes

Reaction equation

HRID 1184384 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:24][CH2:25][CH:26]3[CH2:28][CH2:27]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)=[O:14])=[CH:4][CH:3]=1.Cl.[CH3:30][O:31][NH2:32]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18]/[C:17]/2=[N:32]\[O:31][CH3:30])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 67970698HCID 67970698, compound

Product 1

HCID 57378999HCID 57378999, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution under of 100 mg of 5-(4-chloro-phenyl)-6-cyclopropylmethoxy-N-((S)-2-oxo-cyclohexyl)-nicotinamide in 1 ml methanol was added 105 mg O-methylhydroxylamine hydrochloride and the mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate=95:5 to 50:50 to yield 0.039 g of the title compound as white foam. MS (EI): 402.3 (M+H).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-88a7b75abb114e859dec1845babe7a15
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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