HCID 69948166, compound → HCID 178527379, compound

HRID 397642Notes

Reaction equation

Cl.[CH2:2]([C:9]1[O:13][N:12]=[C:11]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:20][C:21]1[CH:33]=[CH:32][C:24]2[NH:25][C:26]([S:28](Cl)(=[O:30])=[O:29])=[N:27][C:23]=2[CH:22]=1>>[CH2:2]([C:9]1[O:13][N:12]=[C:11]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[S:28]([C:26]2[NH:25][C:24]3[CH:32]=[CH:33][C:21]([Br:20])=[CH:22][C:23]=3[N:27]=2)(=[O:30])=[O:29])[N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 69948166HCID 69948166, compound

HCID 178527436HCID 178527436, compound

Product 1

HCID 178527379HCID 178527379, compound

Procedure

The title compound was prepared by a similar method to Example 1 from 5-benzyl-3-[(2S)-2-piperidyl]-1,2,4-oxadiazole hydrochloride [see-Preparation 7] and 5-bromo-1H-benzo[d]imidazole-2-sulfonyl chloride [see Preparation 88]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 70:30, by volume, hexane:ethyl acetate, in 10% increments, to afford 2-[(2S)-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-1-piperidyl]sulfonyl-5-bromo-1H-benzo[d]imidazole as a white solid.

Workup

customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 70:30, by volume, hexane

Sources & evidence

ORD record: ord-f42b929a318d4ba29a73965ce8155d63
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610707B1

Reaction notes

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