Sulfuric 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 sulfate

HRID 1978789Notes

Reaction equation

HRID 1978789 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.[S:45](=[O:49])(=[O:48])([OH:47])[OH:46]>CC(C)=O>[S:45]([OH:49])([OH:48])(=[O:47])=[O:46].[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 1118Sulfuric 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 21995789N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide sulfate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 acetone (150 ml) was added at room temperature 47% sulfuric acid (0.27 ml), and the mixture was stirred for 0.5 hours and concentrated under reduced pressure. To the residue was added 2-propanol, and the mixture was concentrated. To the residue was added 2-propanol, and the resulting solid was collected by filtration and dissolved in 2-propanol under heating. The solution was cooled, and the resulting powder was collected by filtration to give colorless amorphous 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 sulfate (Compound 148) (1.21 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added 2-propanol
  3. concentrationthe mixture was concentrated
  4. additionTo the residue was added 2-propanol
  5. filtrationthe resulting solid was collected by filtration
  6. dissolutiondissolved in 2-propanol
  7. temperatureunder heating
  8. temperatureThe solution was cooled
  9. filtrationthe resulting powder was collected by filtration

Sources & evidence

ORD record
ord-bf96dcb817e34168a7646029e6d97d0f
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

Loading…