Isopropanol → HCID 21995891, compound

HRID 1978643Notes

Reaction equation

HRID 1978643 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][C:16]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:32]([CH3:39])[CH:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[CH:27][CH:26]=4)=[O:23])=[CH:15][C:14]=3[CH:40]=2)=[CH:6][CH:5]=1)[CH3:2].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].CC(O)C>C1COCC1>[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][C:16]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:32]([CH3:39])[CH:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[CH:27][CH:26]=4)=[O:23])=[CH:15][C:14]=3[CH:40]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6395Methanesulfonic AcidHCID 21995680HCID 21995680, compound

Product 1

HCID 21995891HCID 21995891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-ethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (2.5 g) in THF (200 ml) was added at room temperature methane sulfonic acid (0.29 ml), and the mixture was stirred for 0.5 hours. To the mixture was added 2-propanol, and the mixture was concentrated under reduced pressure. Precipitated crystals were dissolved at 90° C. in 2-propanol, and the mixture was cooled to room temperature and then cooled to 0° C. to give crystals, which were collected by filtration and washed with diethylether to give colorless crystals of 7-(4-ethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide methane sulfonate (Compound 58) (2.56 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customPrecipitated crystals
  3. dissolutionwere dissolved at 90° C. in 2-propanol
  4. temperaturecooled to 0° C.
  5. customto give crystals, which
  6. filtrationwere collected by filtration
  7. washwashed with diethylether

Sources & evidence

ORD record
ord-c627e72024694c93b7e436e2a6180d40
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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