Methyl cis-3-hydroxymethylcyclohexanecarboxylate → cis-[3-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-yl)cyclohexyl]methanol

HRID 221367Notes

Reaction equation

HRID 221367 reaction equation
CO[C:3]([C@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([CH2:11][OH:12])[CH2:6]1)=[O:4].O[NH:14][C:15](=[NH:22])[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1>>[N:19]1[CH:20]=[CH:21][C:16]([C:15]2[N:22]=[C:3]([C@@H:5]3[CH2:10][CH2:9][CH2:8][C@H:7]([CH2:11][OH:12])[CH2:6]3)[O:4][N:14]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 57350257Methyl cis-3-hydroxymethylcyclohexanecarboxylateHCID 178513374HCID 178513374, compound

Product 1

HCID 69079864cis-[3-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-yl)cyclohexyl]methanol

Procedure

cis-Methyl-3-hydroxymethylcyclohexane-1-carboxylate was reacted with N-hydroxy-isonicotinamidine, using the reaction conditions described in Preparation 5, to afford cis-[3-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)cyclohexyl]methanol: RT=2.70 min, m/z (ES+)=246.1 [M+H]+. This was subsequently alkylated with 1-bromobutane, under similar conditions to those described in Example 106, to afford the title compound: RT=4.11 min, m/z (ES+)=316.3 [M+H]+.

Workup

  1. customthe reaction conditions
  2. customdescribed in Preparation 5

Sources & evidence

ORD record
ord-6bbe576c44db4766aea378e1fddd8d0f
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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