3-(4-Tert-butylphenyl)-5-(chloromethyl)-1,2,4-oxadiazole → (2S)-3-[4-({3-[4-(tert-butyl)phenyl](1,2,4-oxadiazol-5-yl)}methyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol

HRID 891051

Reaction equation

HRID 891051 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@@H:13]([OH:21])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH2:37]Cl)[O:34][N:33]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>CN(C)C.C(O)C>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:36]=[C:35]([CH2:37][N:18]3[CH2:17][CH2:16][N:15]([CH2:14][C@H:13]([OH:21])[CH2:12][O:11][C:8]4[CH:9]=[CH:10][C:4]5[S:3][C:2]([CH3:1])=[N:6][C:5]=5[CH:7]=4)[CH2:20][CH2:19]3)[O:34][N:33]=2)=[CH:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 27817013-(4-Tert-butylphenyl)-5-(chloromethyl)-1,2,4-oxadiazoleHCID 58595334(2S)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Product 1

HCID 23598931(2S)-3-[4-({3-[4-(tert-butyl)phenyl](1,2,4-oxadiazol-5-yl)}methyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 86589564Trimethylamine ethanolSolvent

Procedure

A solution of (2S)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol, a compound of formula (6) (75 mg, 0.14 mmol), and 3-(4-tert-butylphenyl)-5-chloromethyl-1,2,4-oxadiazole (40 mg, 0.16 mmol) in 10% trimethylamine/ethanol, was heated to 73° C. and allowed to stir overnight. The solvent was evaporated under reduced pressure, and the resulting residue chromatographed by PTLC (3% methanol/methylene chloride). The resulting oil was diluted with methylene chloride and placed on the high Vac. overnight, to yield (2S)-3-[4-({3-[4-(tert-butyl)phenyl](1,2,4-oxadiazol-5-yl)}methyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol as a white solid (52 mg, 0.09 mmol).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue chromatographed by PTLC (3% methanol/methylene chloride)
  3. additionThe resulting oil was diluted with methylene chloride

Sources & evidence

ORD record
ord-9cf47494fad346a0bd0c93ea433dbbe1
Source dataset
uspto-grants-2006_02
Patent number
US07001909B2

Linked notes

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