O-Methylhydroxylamine hydrochloride → 4-(1-(5-Chloro-2-(3-((3-fluorophenyl)(methoxyimino)methyl)azetidin-1-yl)nicotinamido)cyclopropyl) benzoic acid

HRID 72549Notes

Reaction equation

HRID 72549 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:23]2[CH2:26][CH:25]([C:27](=O)[C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)[CH2:24]2)=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].Cl.[CH3:37][O:38][NH2:39]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:23]2[CH2:26][CH:25]([C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[N:39][O:38][CH3:37])[CH2:24]2)=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:20][CH:21]=2)[CH2:11][CH2:12]1)=[O:8]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 57378225HCID 57378225, compound

Product 1

HCID 765304394-(1-(5-Chloro-2-(3-((3-fluorophenyl)(methoxyimino)methyl)azetidin-1-yl)nicotinamido)cyclopropyl) benzoic acidYield 22.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(1-(5-chloro-2-(3-(3-fluorobenzoyl)azetidin-1-yl)nicotinamido)cyclopropyl)benzoic acid (E25) (12.6 mg, 0.025 mmol) was dissolved in dry pyridine (1.2 ml) then O-methylhydroxylamine hydrochloride (4.3 mg, 0.051 mmol) was added and the resulting mixture was stirred at room temperature for 60 h. Solvents were evaporated in vacuo, and the residue was diluted with water (5 ml) and extracted with ethylacetate (3×20 ml). Collected organics, after solvent evaporation, afforded a residue that was washed with methanol and dried in vacuo to afford the title compound (E26) (D021/092/2) (3 mg).

Workup

  1. customSolvents were evaporated in vacuo
  2. additionthe residue was diluted with water (5 ml)
  3. extractionextracted with ethylacetate (3×20 ml)
  4. customCollected organics, after solvent evaporation
  5. customafforded a residue that
  6. washwas washed with methanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c3d7c6b4b75f47ed8e702c3a4fe3ca59
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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