Hydrochloric Acid → HCID 59003169, compound

HRID 2353866Notes

Reaction equation

HRID 2353866 reaction equation
Cl.[C:2]([N:5]([CH2:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=1)[CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:8]2[CH:19]=[CH:20][C:21]([N:23]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:22][C:7]1=2)(=[O:4])[CH3:3]>O1CCCC1.C(OCC)(=O)C>[C:2]([N:5]([CH2:37][C:38]1[CH:39]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:41]=[C:42]([C:44]([F:47])([F:45])[F:46])[CH:43]=1)[CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:8]2[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:7]1=2)(=[O:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86616063HCID 86616063, compound

Product 1

HCID 59003169HCID 59003169, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 2 N hydrochloric acid (2 mL) to a solution of isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-(benzhydrylideneamino)-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (example 6b) (0.920 g, 1.32 mmol) in tetrahydrofuran (10 mL) at room temperature and stir for 15 min. Dilute the mixture with ethyl acetate (20 mL) and wash with saturated sodium hydrogen carbonate solution and brine (10 mL each). Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (1:1), to provide the title compound as an off-white solid (0.526 g, 75%); APCI MS 531 (M+H).

Workup

  1. washwash with saturated sodium hydrogen carbonate solution and brine (10 mL each)
  2. dry with materialDry the organic layer over anhydrous sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. washChromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c59c2f7cf77e4c8eaae6c0b8ce53b3fc
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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