Potassium bisulfate → HCID 53372241, compound

HRID 340783Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[OH:41])=[CH:31][CH:30]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH:11]3[CH2:14][CH:13]([C:15]([O:17]CC)=[O:16])[CH2:12]3)[N:7](COCC[Si](C)(C)C)[C:6]=2[CH:28]=1.S(=O)(=O)(O)[O-].[K+]>C(O)=O>[Cl:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[OH:41])=[CH:31][CH:30]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH:11]3[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12]3)[NH:7][C:6]=2[CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 3-{[6-chloro-5-(2′-hydroxybiphenyl-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl]oxy}cyclobutanecarboxylate (153 mg, 0.258 mmol) in formic acid (4 mL) was added saturated aqueous solution of potassium bisulfate (0.8 ml, 0.258 mmol). The reaction mixture was heated at 80° C. overnight. Then the volatiles were removed in vacuo, and the residue acidified with 1 N aqueous HCl, and extracted with EtOAc. The organic phase was separated, washed with water, and concentrated in vacuo. Purification of the resulting residue by reverse phase HPLC (20-100% MeCN: H2O) afforded the title compound as a white solid. LC-MS: calculated for C24H19ClN2O4 434.1, observed m/e: 434.99 (M+H)+ (Rt 1.82/4 min). 1H NMR (500 MHz, CD3OD): δ 7.70-6.90 (m, 10H), 5.25-5.20 (m, 1H), 2.90 (m, 3H) 2.50 (m, 2H).

Workup

customThen the volatiles were removed in vacuo
extractionextracted with EtOAc
customThe organic phase was separated
washwashed with water
concentrationconcentrated in vacuo
customPurification of the resulting residue by reverse phase HPLC (20-100% MeCN: H2O)

Sources & evidence

ORD record: ord-dd2860bab39048939c2629a545ff0b50
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895596B2

Reaction notes

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