Hydrochloric Acid → HCID 178494499, compound

HRID 2401988Notes

Reaction equation

HRID 2401988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:12][C:11]=2[C:21]2[NH:25][CH:24]=[N:23][N:22]=2)[OH:9])=[CH:4][CH:3]=1.Cl.[CH3:27]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:9][CH3:27])[C:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)[S:12][C:11]=2[C:21]2[NH:25][CH:24]=[N:23][N:22]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178519583HCID 178519583, compound

Product 1

HCID 178494499HCID 178494499, compoundYield 78%

Procedure

To a solution of (4-chlorophenyl)[5-pyridin-4-yl-2-(4H-1,2,4-triazol-3-yl)-3-thienyl]methanol (100 mg, 0.271 mmol) in methanol (10 mL) was added conc. HCl (2.0 mL, 24 mmol) and the mixture was stirred at rt overnight. The reaction mixture was concentrated and basified by sodium bicarbonate, loaded on silica gel and purified by column chromatography (SiO2, elution with 0-5% MeOH in DCM) to afford the title compound (80 mg, 78%). LCMS: (AA) ES+ 383.3, 385.2; 1H NMR (300 MHz, d6-DMSO) δ: 8.70 (s, 1H), 8.57 (d, J=4.80 Hz, 2H), 7.79 (s, 1H), 7.68 (d, J=4.79 Hz, 2H), 7.56 (d, J=8.25 Hz, 2H), 7.38 (d, J=8.30 Hz, 2H), 6.50 (s, 1H), 3.31 (d, J=9.06 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography (SiO2, elution with 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-e9197798cb7c4a87af2bd995b4f7d461
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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