(S)-methyl 2-(piperidin-3-yl)acetate hydrochloride → (R)-2-(1-(5-(Cyclohexylcarbamoyl)-3-fluoro-6-(propylthio)pyridin-2-yl)piperidin-3-yl)acetic acid

HRID 2424924Notes

Reaction equation

HRID 2424924 reaction equation
Cl[C:2]1[C:16]([F:17])=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([S:18][CH2:19][CH2:20][CH3:21])[N:3]=1.Cl.[NH:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([CH2:29][C:30]([O:32]C)=[O:31])[CH2:24]1>>[CH:9]1([NH:8][C:6]([C:5]2[CH:15]=[C:16]([F:17])[C:2]([N:23]3[CH2:28][CH2:27][CH2:26][C@H:25]([CH2:29][C:30]([OH:32])=[O:31])[CH2:24]3)=[N:3][C:4]=2[S:18][CH2:19][CH2:20][CH3:21])=[O:7])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 45073966(S)-methyl 2-(piperidin-3-yl)acetate hydrochlorideHCID 598306576-chloro-N-cyclohexyl-5-fluoro-2-(propylthio)nicotinamide

Product 1

HCID 59830628(R)-2-(1-(5-(Cyclohexylcarbamoyl)-3-fluoro-6-(propylthio)pyridin-2-yl)piperidin-3-yl)acetic acid

Procedure

Prepared in a similar manner to that described above from 6-chloro-N-cyclohexyl-5-fluoro-2-(propylthio)nicotinamide using (S)-methyl 2-(piperidin-3-yl)acetate hydrochloride followed by an ester hydrolysis as described above to give the desired compound (190 mg) as a white solid.

Workup

  1. customPrepared in a similar manner to that

Sources & evidence

ORD record
ord-6c770d5b5c094bc8852310230112399a
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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