(1E)-N'-Hydroxy-3-methoxypropanimidamide hydrochloride → HCID 58002258, compound

HRID 1643089Notes

Reaction equation

HRID 1643089 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]([NH2:34])[CH2:30][CH2:31][O:32][CH3:33]>>[CH3:33][O:32][CH2:31][CH2:30][C:29]1[N:34]=[C:24]([CH:10]2[CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=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 4390391(1E)-N'-Hydroxy-3-methoxypropanimidamide hydrochlorideHCID 58002663HCID 58002663, compound

Product 1

HCID 58002258HCID 58002258, compoundYield 24%

Procedure

250 mg (0.644 mmol) of 1-(1,3-thiazolidin-3-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 102A) and 112 mg (0.708 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 35.0 mg of the title compound from Example 317 and 38.0 mg of the title compound from Example 318 (24% of theory).

Workup

  1. customEnantiomer separation of the racemate

Sources & evidence

ORD record
ord-f06033cf4e5b49c8a3c5bf5f8953a478
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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