N-Hydroxyacetamidine → HCID 58002644, compound

HRID 1643083Notes

Reaction equation

HRID 1643083 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-0dfb7f423f1549f69a3467322a5486e7
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

Loading…