Hydrochloric Acid → HCID 86624193, compound

HRID 1191160Notes

Reaction equation

HRID 1191160 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2(OCC[O:35]2)[CH2:28][S:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[CH:23][CH:22]=1.Cl>ClCCl.O1CCOCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH2:28][S:29][CH2:30][C:31]([F:34])([F:32])[F:33])=[O:35])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86624192HCID 86624192, compound

Product 1

HCID 86624193HCID 86624193, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-chloro-3-(2,2,2-trifluoroacetyl)-6-{4-[2-(2,2,2-trifluoroethylthio)-1,1-(ethylenedioxy)ethyl]-benzylamino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (97 mg, 0.16 mmol) in anhydrous dichloromethane (0.5 mL), add a solution of 4M hydrogen chloride in dioxane (1.2 mL) and reflux overnight. Dilute with dichloromethane and wash with saturated aqueous NaHCO3. Dry the organics extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain 7-chloro-3-(2,2,2-trifluoroacetyl)-6-[4-(2,2,2-trifluoroethylthio-methylcarbonyl)-benzylamino]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (37 mg, 41%). MS (ES+) m/z: 539 (M+H)+.

Workup

  1. temperaturereflux overnight
  2. washwash with saturated aqueous NaHCO3
  3. dry with materialDry the organics extracts over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-ebc872eb935c4b2cbb8204f2f923d794
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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