(1E)-N'-Hydroxy-3-methoxypropanimidamide hydrochloride → HCID 58002393, compound

HRID 1643049Notes

Reaction equation

HRID 1643049 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:26]([OH:28])=O)[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.O[N:30]=[C:31]([NH2:36])[CH2:32][CH2:33][O:34][CH3:35]>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=3)[CH2:13][CH:12]([C:26]3[O:28][N:36]=[C:31]([CH2:32][CH2:33][O:34][CH3:35])[N:30]=3)[CH2:11]2)=[O:9])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 4390391(1E)-N'-Hydroxy-3-methoxypropanimidamide hydrochlorideHCID 580023401-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002393HCID 58002393, compoundYield 36%

Procedure

250 mg (0.624 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 99A) and 108 mg (0.687 mmol, 75% pure) of N′-hydroxy-3-methoxypropanimidamide (Example 64A) were reacted according to the General Method 1. Enantiomer separation of the racemate according to Method 16D gave 56.0 mg of the title compound from Example 275 and 55.0 mg of the title compound from Example 276 (36% of theory).

Workup

  1. customEnantiomer separation of the racemate

Sources & evidence

ORD record
ord-b9e6c69d240a42ca8bb5bceb8948c487
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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