Potassium bisulfate → HCID 53372375, compound

HRID 340781Notes

Reaction equation

[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:33]([Cl:34])=[CH:32][C:10]3[N:11](COCC[Si](C)(C)C)[C:12]([O:14][CH:15]4[CH2:18][CH:17]([C:19]([O:21]CC)=[O:20])[CH2:16]4)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.S(=O)(=O)(O)[O-].[K+]>C(O)=O>[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:33]([Cl:34])=[CH:32][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:18][CH:17]([C:19]([OH:21])=[O:20])[CH2:16]4)=[N:13][C:9]=3[CH:8]=2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 3-{[5-(biphenyl-4-yl)-6-chloro-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl]oxy}cyclobutanecarboxylate (100 mg, 0.173 mmol) in formic acid (1.7 ml) was added a saturated aqueous solution of potassium bisulfate (0.3 ml, 0.173 mmol). The reaction mixture was heated at 80° C. for 1 h. Then the volatiles were removed in vacuo and the resulting residue was acidified with 1N 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 eluting with 30-100% MeCN:H2O afforded the title compound as a white solid. LC-MS: calculated for C24H19ClN2O3 418.11, observed m/e: 418.93 (M+H)+ (Rt 2.16/4 min). 1H NMR (500 MHz, CD3OD): δ 7.75-7.35 (m, 11H), 5.25-5.20 (m, 1H), 2.90 (m, 31-1) 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
washeluting with 30-100% MeCN

Sources & evidence

ORD record: ord-e98b71410cf7476dbf0ef57fcc8734f4
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895596B2

Reaction notes

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