Hydrochloric Acid → HCID 178442239, compound

HRID 425369Notes

Reaction equation

Cl.[CH3:2][C:3]([CH3:32])([CH3:31])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:30])([CH3:29])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:20][CH:19]=2)[N:8](S(N(C)C)(=O)=O)[CH:9]=1>CO>[CH3:2][C:3]([CH3:32])([CH3:31])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:30])([CH3:29])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:20][CH:19]=2)[NH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (0.25 mL, 1 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-{1-hydroxy-1-methyl-2-[4-(1H-pyrazol-1-yl)phen yl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (25 mg, 0.06 mmol) in methanol (2 mL). After stirring at 80° C. for 2 h, volatiles were removed in vacuo. The residue was partitioned between 1 N hydrochloric acid and diethyl ether. The aqueous phase was basified with 4 N aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to afford the title compound. Chiral HPLC eluting with IPA/heptane afforded the two individual enantiomers. 1H NMR (500 MHz, CD3OD) δ 7.84 (s, 1H), 7.7 (s, 1H), 7.5 (d, J=7 Hz, 2H), 7.05 (d, J=7 Hz, 2H), 6.6 (s, 1H), 6.4 (s, 1H), 3.35 (d, J=12 Hz, 1H), 3.05 (d, J=12 Hz, 1H), 2.40 (s, 2H), 1.63 (s, 3H), 0.85 (s, 9H); (M+H) found: 339.

Workup

customvolatiles were removed in vacuo
customThe residue was partitioned between 1 N hydrochloric acid and diethyl ether
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried (sodium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b96c7cd7396847a9a5f0db296c32a4c8
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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