5-Thiazoleacetic acid, 2,4-dimethyl- → (S)-1-(2-benzyl-4-(3-cyclobutoxy-4-methoxyphenyl)piperazin-1-yl)-2-(2,4-dimethylthiazol-5-yl)ethanone

HRID 1423160Notes

Reaction equation

HRID 1423160 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:8][C:9]([OH:11])=O)=[C:5]([CH3:7])[N:6]=1.[CH2:12]([C@@H:19]1[NH:24][CH2:23][CH2:22][N:21]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]3[CH2:37][CH2:36][CH2:35]3)[CH:26]=2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([C@H:19]1[CH2:20][N:21]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]3[CH2:37][CH2:36][CH2:35]3)[CH:26]=2)[CH2:22][CH2:23][N:24]1[C:9](=[O:11])[CH2:8][C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[CH3:7])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 2147995-Thiazoleacetic acid, 2,4-dimethyl-HCID 58188985HCID 58188985, compound2×

Product 1

HCID 58189186(S)-1-(2-benzyl-4-(3-cyclobutoxy-4-methoxyphenyl)piperazin-1-yl)-2-(2,4-dimethylthiazol-5-yl)ethanone

Procedure

Prepared by the method outlined for Example 189 using (2,4-dimethyl-thiazol-5-yl)-acetic acid and 3(S)-benzyl-1-(3-cyclobutoxy-4-methoxy-phenyl)-piperazine (Example 7, Compound 95) as starting materials to afford product as an oil. LC/MS (Method B) 2.46 min, [M+1]+ 505. Potency class B.

Workup

  1. customPrepared by the method
  2. customto afford product as an oil
  3. customLC/MS (Method B) 2.46 min, [M+1]+ 505

Sources & evidence

ORD record
ord-598df0e15a0e478c82c1e898bf775f34
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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