N-Hydroxyacetamidine → HCID 58002475, compound

HRID 1643086Notes

Reaction equation

HRID 1643086 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH2:11][CH:10]([C:24](O)=[O:25])[CH2:9]2)=[O:7])[CH2:2]1.O[N:28]=[C:29]([NH2:31])[CH3:30]>>[CH3:30][C:29]1[N:31]=[C:24]([CH:10]2[CH2:11][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)[CH2:13][N:8]([C:6]([N:3]3[CH2:4][CH2:5][S:1][CH2:2]3)=[O:7])[CH2:9]2)[O:25][N:28]=1

Participants

3

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 58002663HCID 58002663, compound

Product 1

HCID 58002475HCID 58002475, compoundYield 29%

Procedure

250 mg (0.644 mmol) of 1-(1,3-thiazolidin-3-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 102A) and 52.5 mg (0.708 mmol) of N′-hydroxyethanimidamide were reacted according to the General Method 1. Enantiomer separation of the racemate according to Method 16D gave 38.0 mg of the title compound from Example 315 and 41.0 mg of the title compound from Example 316 (29% of theory).

Workup

  1. customEnantiomer separation of the racemate

Sources & evidence

ORD record
ord-3ec269b986ba4ef493e701c8d7015b5d
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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