Potassium ethanethioate → HCID 178467360, compound

HRID 1510981Notes

Reaction equation

Cl[CH2:2][CH:3]([NH:8][C:9]([C:11]1[C:19]2[N:18]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:17]([O:38][CH2:39][CH3:40])=[N:16][C:15]=2[CH:14]=[CH:13][CH:12]=1)=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6].[C:41]([O-:44])(=[S:43])[CH3:42].[K+]>CC#N>[CH2:39]([O:38][C:17]1[N:18]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)[C:19]2[C:11]([C:9]([NH:8][CH:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][S:43][C:41](=[O:44])[CH3:42])=[O:10])=[CH:12][CH:13]=[CH:14][C:15]=2[N:16]=1)[CH3:40]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Ethoxy-3-[2′-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid (1-chloromethyl-3-methylbutyl)amide (100 mg, 180 μmol) and potassium thioacetate (31 mg, 15 equiv) were dissolved in MeCN (5 mL) and heated at 90° C. overnight. The solvent was evaporated and the residue partitioned between water (10 mL) and EtOAc (10 mL). The aqueous phase was discarded, the organic layer washed with saturated aqueous NaCl, dried over NaSO4, decanted, and the solvent evaporated. The crude product (80 mg, 70%) was used without further purification. ESMS [M+H]+ calcd for C32H35N7O3S, 597.3. found 598.3.

Workup

customThe solvent was evaporated
customthe residue partitioned between water (10 mL) and EtOAc (10 mL)
washthe organic layer washed with saturated aqueous NaCl
dry with materialdried over NaSO4
customdecanted
customthe solvent evaporated
customThe crude product (80 mg, 70%) was used without further purification

Sources & evidence

ORD record: ord-067e6c9077b04800970aa8bdb8bdbc93
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212052B2

Reaction notes

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