N-Hydroxyacetamidine → HCID 58002644, compound

HRID 1643082Notes

Reaction equation

HRID 1643082 reaction equation
[CH3:1][O:2][CH:3]1[CH2:6][N:5]([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:25](O)=[O:26])[CH2:10]2)=[O:8])[CH2:4]1.O[N:29]=[C:30]([NH2:32])[CH3:31]>>[CH3:1][O:2][CH:3]1[CH2:6][N:5]([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:25]3[O:26][N:32]=[C:30]([CH3:31])[N:29]=3)[CH2:10]2)=[O:8])[CH2:4]1

Participants

3

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 58002494HCID 58002494, compound

Product 1

HCID 58002644HCID 58002644, compoundYield 50%

Procedure

250 mg (0.647 mmol) of 1-[(3-methoxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 103A) and 52.7 mg (0.712 mmol) of N′-hydroxyethanimidamide were reacted according to the General Method 1. Enantiomer separation of the racemate according to Method 16D gave 73.0 mg of the title compound from Example 311 and 64.0 mg of the title compound from Example 312 (50% of theory).

Workup

  1. customEnantiomer separation of the racemate

Sources & evidence

ORD record
ord-9a91a863bfa34c94b210a3e642ac1cfa
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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