Hydrochloric Acid → HCID 178482562, compound

HRID 1808150Notes

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

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 (non-polar diastereomer) (200 mg, 0.38 mmol) in methanol (10 mL) was mixed with 37% hydrochloric acid (10 mL) and stirred for 7 h at 100° C. in a Teflon pressure vessel. Methanol (10 mL) and 37% hydrochloric acid (10 mL) was then added again and the mixture stirred a further 6 h at 100° C. The reaction solution was then concentrated to low volume in a vacuum and the residue (250 mg) purified by flash chromatography (37 g, 20×2.1 cm) with dichloromethane/methanol [8:2+1% NH3 (32% in H2O)].

Workup

stirringthe mixture stirred a further 6 h at 100° C
concentrationThe reaction solution was then concentrated to low volume in a vacuum
customthe residue (250 mg) purified by flash chromatography (37 g, 20×2.1 cm) with dichloromethane/methanol [8:2+1% NH3 (32% in H2O)]

Sources & evidence

ORD record: ord-320d73cebfce44468fd06c3ce33db218
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357705B2

Reaction notes

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