Benzenesulfonic Acid → 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 benzenesulfonate

HRID 1978788Notes

Reaction equation

HRID 1978788 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.[C:45]1([S:51]([OH:54])(=[O:53])=[O:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[C:45]1([S:51]([OH:54])(=[O:53])=[O:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[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 7371Benzenesulfonic AcidHCID 3009396N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide

Product 1

HCID 21995841N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide benzenesulfonateYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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 (1.10 g) in THF (40 ml) was added at room temperature benzenesulfonic acid (313 mg), and the mixture was stirred for 1 hour and concentrated under reduced pressure. To the residue was added 2-propanol, and the mixture was concentrated under reduced pressure. The residue was crystallized from 2-propanol to give crude crystals, which were recrystallized from 2-propanol to give colorless crystals of 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 benzenesulfonate (Compound 147) (1.19 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added 2-propanol
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was crystallized from 2-propanol
  5. customto give crude crystals, which
  6. customwere recrystallized from 2-propanol

Sources & evidence

ORD record
ord-5824fae4ab7a4e5280a1550c4550e57d
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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