Hydrochloric Acid → HCID 21995864, compound

HRID 1978555Notes

Reaction equation

HRID 1978555 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][CH:6]([N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]4[CH2:22][CH2:23][S:24](=[O:41])(=[O:40])[C:25]5[CH:31]=[CH:30][C:29]([C:32]6[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=6)=[CH:28][C:26]=5[CH:27]=4)=[O:20])=[CH:14][CH:13]=3)[CH3:10])[CH2:5][CH2:4]2)[O:2]1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:30]=[CH:31][C:25]3[S:24](=[O:40])(=[O:41])[CH2:23][CH2:22][C:21]([C:19]([NH:18][C:15]4[CH:16]=[CH:17][C:12]([CH2:11][N:9]([CH3:10])[CH:6]5[CH2:5][CH2:4][C:3](=[O:2])[CH2:8][CH2:7]5)=[CH:13][CH:14]=4)=[O:20])=[CH:27][C:26]=3[CH:28]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21995792HCID 21995792, compound

Product 1

HCID 21995864HCID 21995864, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-7-(4-methoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (112 mg) in THF (20 ml) was added at room temperature 3N hydrochloric acid (1 ml), and the mixture was stirred for 18 hours. To the mixture was added saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give colorless solid, which was recrystallized from ethyl acetate/hexane to give colorless crystals of 7-(4-methoxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 17) (77.6 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give colorless solid, which
  6. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-416d99a869eb4bc681996e17558ca1f9
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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