Hydrochloric Acid → HCID 178482562, compound

HRID 1808152Notes

Reaction equation

HRID 1808152 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([N:17]([CH:24]2[CH2:29][CH2:28][C:27]([N:36]([CH3:38])[CH3:37])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)C(=O)C(F)(F)F)[C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:2]1.Cl>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([NH:17][CH:24]2[CH2:29][CH2:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([N:36]([CH3:38])[CH3:37])[CH2:26][CH2:25]2)[C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178482563HCID 178482563, compound

Product 1

HCID 178482562HCID 178482562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of N-(2-(1H-indol-3-yl)-1-(1H-tetrazol-5-yl)ethyl)-N-(4-dimethylamino-4-phenylcyclohexyl)-2,2,2-trifluoroacetamide (100 mg, 0.19 mmol) in methanol (10 mL) was mixed with 37% hydrochloric acid (3 mL) and stirred for 7 h at 100° C. in a Teflon pressure vessel. 37% hydrochloric acid (3 mL) was then added again, the mixture stirred for a further 24 h at 100° C. and then concentrated to low volume in a vacuum. The raw product was purified by flash chromatography (85 g, 20×3.6 cm) with dichloromethane/methanol [2:1+1% NH3 (32% in H2O)].

Workup

  1. stirringthe mixture stirred for a further 24 h at 100° C.
  2. concentrationconcentrated to low volume in a vacuum
  3. customThe raw product was purified by flash chromatography (85 g, 20×3.6 cm) with dichloromethane/methanol [2:1+1% NH3 (32% in H2O)]

Sources & evidence

ORD record
ord-c25883c318594398805d82fa02ddbdf6
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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