Hydrochloric Acid → 3-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol

HRID 244477Notes

Reaction equation

HRID 244477 reaction equation
Cl.CC1(C)[O:7][CH:6]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]([C:24]3[CH:39]=[CH:38][C:27]4[N:28]([C:31]5[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=5)[N:29]=[N:30][C:26]=4[CH:25]=3)([OH:23])[C:19]([F:22])([F:21])[F:20])=[CH:10]2)[CH2:5][O:4]1>C(#N)C>[F:21][C:19]([F:20])([F:22])[C:18]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([CH2:8][CH:6]([OH:7])[CH2:5][OH:4])[CH:10]=1)([C:24]1[CH:39]=[CH:38][C:27]2[N:28]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[N:29]=[N:30][C:26]=2[CH:25]=1)[OH:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594372331-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]ethanol

Product 1

HCID 594372473-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At room temperature, approximately 200 μL of concentrated HCl was added to 1-[1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]ethanol (100 mg) in aqueous acetonitrile. After 90 minutes, LCMS showed one peak MS m/z 501 (MH+) for the desired product. The mixture was then concentrated and the residue diluted with sodium bicarbonate and extracted with ethyl acetate. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 95 mg of the title compound as an off-white solid.

Sources & evidence

ORD record
ord-75565fcc203a4c49b6b5ab4b12728384
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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