N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide → N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide hydrochloride

HRID 1978720Notes

Reaction equation

HRID 1978720 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[CH2:20][CH2:21][S:22](=[O:44])(=[O:43])[C:23]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH3:42])=[CH:32][CH:31]=4)=[CH:26][C:24]=3[CH:25]=2)=[O:18])=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[ClH:45].C(OCC)(=O)C>C1COCC1>[ClH:45].[CH3:1][N:2]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]([C:19]2[CH2:20][CH2:21][S:22](=[O:44])(=[O:43])[C:23]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH3:42])=[CH:34][CH:35]=4)=[CH:26][C:24]=3[CH:25]=2)=[O:18])=[CH:14][CH:15]=1)[CH:3]1[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 3009396N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 21995696N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (850 ml) was dissolved N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (17.3 g), and to the mixture was added at room temperature 4N hydrochloric acid/ethyl acetate (14 ml). The mixture was stirred for 1 hour. Under reduced pressure, the solvent was evaporated, and the residue was washed with ethyl acetate/acetone and recrystallized from ethanol to give N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide hydrochloride (Compound 112) (11.2 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. washthe residue was washed with ethyl acetate/acetone
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-40d1f96fe6a14c879ed933c474e837e3
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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