2-(3-methyl-1H-1,2,4-triazol-5-yl)acetic acid → (S)-1-(2-benzyl-4-(3-cyclobutoxy-4-(difluoromethoxy)phenyl)piperazin-1-yl)-2-(5-methyl-1H-1,2,4-triazol-3-yl)ethanone

HRID 1423174Notes

Reaction equation

HRID 1423174 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][C:8]([OH:10])=O)[N:3]=1.[CH2:11]([C@@H:18]1[NH:23][CH2:22][CH2:21][N:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH:35]3[CH2:38][CH2:37][CH2:36]3)[CH:25]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:19][N:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:32])[F:33])=[C:26]([O:34][CH:35]3[CH2:38][CH2:37][CH2:36]3)[CH:25]=2)[CH2:21][CH2:22][N:23]1[C:8](=[O:10])[CH2:7][C:4]1[N:3]=[C:2]([CH3:1])[NH:6][N:5]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 70194772-(3-methyl-1H-1,2,4-triazol-5-yl)acetic acidHCID 58189227HCID 58189227, compound2×

Product 1

HCID 58189125(S)-1-(2-benzyl-4-(3-cyclobutoxy-4-(difluoromethoxy)phenyl)piperazin-1-yl)-2-(5-methyl-1H-1,2,4-triazol-3-yl)ethanone

Procedure

Prepared by the method outlined for Example 189 using (5-methyl-1H-[1,2,4]triazol-3-yl)-acetic acid and (S)3-benzyl-1-(3-cyclobutoxy-4-difluoromethoxy-phenyl)-piperazine (Example 4, Compound 92) as starting materials. Product as an oil. LC/MS (Method B) 2.66 min, [M+1]+ 512. Potency class A.

Workup

  1. customPrepared by the method
  2. customLC/MS (Method B) 2.66 min, [M+1]+ 512

Sources & evidence

ORD record
ord-cf6a678add934999a313360d454086e5
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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