Ethyl Acetate → HCID 42597939, compound

HRID 409386Notes

Reaction equation

HRID 409386 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6](C)[C:7](=[O:29])[CH:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([CH2:27][CH3:28])[CH:20]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(OCC)(=O)C>C1(OC)C=CC=CC=1.C(#N)C.O>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([CH2:27][CH3:28])[CH:20]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 66741757HCID 66741757, compound

Product 1

HCID 42597939HCID 42597939, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 7519AnisoleSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of (Z)-7-chloro-3-(3,4-diethylbenzyl)-5-(4-fluorophenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one (0.1 g, 0.18 mmol) in anisole (3 mL) was added aluminum chloride (0.144 g, 1.08 mmol). The mixture was heated at 85° C. for 1 hour, cooled to ambient temperature and poured into a mixture of ice/water (10 mL) and ethyl acetate (20 mL) and stirred vigorously for 10 min. The layers were separated and the organic phase was dried over sodium sulfate, filtered, and then concentrated. The residue was purified by chromatography (silica gel, 95:5 CH2Cl2:MeOH) to provide an oil which was dissolved in a mixture of acetonitrile (3 mL) and water (1 mL). This solution was freeze-dried overnight to give (Z)-7-chloro-3-(3,4-diethylbenzyl)-5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one as an off-white solid: mp 88-90° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.71 (s, 1H), 7.64 (dd, J=8.8, 2.5 Hz, 1H), 7.49 (t, J=5.6 Hz, 2H), 7.30-7.23 (m, 4H), 7.13-7.01 (m, 3H), 3.65 (t, J=5.5 Hz, 1H), 3.32-3.31 (m, 2H), 2.56 (quintet, J=7.3 Hz, 4H), 1.13 (q, J=7.2 Hz, 6H); APCI MS m/z 435 [M+H+].

Workup

  1. temperaturecooled to ambient temperature
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 95:5 CH2Cl2:MeOH)
  7. customto provide an oil which
  8. customThis solution was freeze-dried overnight

Sources & evidence

ORD record
ord-dd35d174fdc94d1bb19b6570e3b82ef3
Source dataset
uspto-grants-2014_06
Patent number
US08759340B2

Reaction notes

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