Hydrochloric Acid → HCID 86692005, compound

HRID 1505734Notes

Reaction equation

[Si](OCC[CH:11]1[N:22]2[C:23]3[C:19]([CH:20]=[CH:21]2)=[C:18]([C:24]([F:27])([F:26])[F:25])[C:17]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:16][C:15]=3[CH2:14][NH:13][CH2:12]1)(C(C)(C)C)(C)C.Cl.C1C[O:40][CH2:39][CH2:38]1>>[CH2:28]([C:17]1[C:18]([C:24]([F:26])([F:25])[F:27])=[C:19]2[C:23]3=[C:15]([CH2:14][NH:13][CH:12]([CH2:38][CH2:39][OH:40])[CH2:11][N:22]3[CH:21]=[CH:20]2)[CH:16]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8028Tetrahydrofuran

HCID 86692004HCID 86692004, compound

Product 1

HCID 86692005HCID 86692005, compound

Procedure

To a mixture of 2-(2-((tert-butyldimethylsilyl)oxy)ethyl-6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (107 mg, 0.21 mmol) in THF was added conc. HCl (2 mL) at 0° C. and the resulting mixture stirred for 1 h. Purification by reverse-phase chromatography (25→90% CH3CN—H2O-TFA) yielded 2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethanol (50 mg).

Workup

customPurification by reverse-phase chromatography (25→90% CH3CN—H2O-TFA)

Sources & evidence

ORD record: ord-2c8925c195da4c6e82ba0a3224a01b4e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216998B2

Reaction notes

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