Acetoxyacetyl chloride → 2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl acetate

HRID 1505730Notes

Reaction equation

[CH2:1]([C:9]1[C:10]([C:22]([F:25])([F:24])[F:23])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:26]([O:29][CH2:30][C:31](Cl)=[O:32])(=[O:28])[CH3:27].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:26]([O:29][CH2:30][C:31](=[O:32])[CH:20]1[NH:19][CH2:18][C:16]2=[C:15]3[C:11](=[C:10]([C:22]([F:25])([F:24])[F:23])[C:9]([CH2:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:17]2)[CH:12]=[CH:13][N:14]3[CH2:21]1)(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 53 mg, 0.14 mmol) in CH2Cl2 at 0° C. was added 2-acetoxyacetyl chloride (19 mg, 0.14 mmol) and diisopropylethylamine (0.072 mL, 0.42 mmol) and the resulting mixture stirred at 0° C. Upon completion of the reaction completion, the solvent was evaporated and the resulting residue triturated with methanol-diethyl ether to yield 2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl acetate (20 mg) as a white solid.

Workup

customUpon completion of the reaction completion, the solvent was evaporated
customthe resulting residue triturated with methanol-diethyl ether

Sources & evidence

ORD record: ord-909fb72b28ff4dddbbb31feffd349b4f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216998B2

Reaction notes

Loading…