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Triethylamine → 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

HRID 1978705
Notes
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Reaction equation

HRID 1978705 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][C:20]([C:26](O)=[O:27])=[CH:19][C:18]=3[CH:29]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3].S(Cl)(Cl)=O.[CH3:34][N:35]([CH2:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1)[CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.O>[CH3:34][N:35]([CH2:42][C:43]1[CH:44]=[CH:45][C:46]([NH:47][C:26]([C:20]2[CH2:21][CH2:22][S:23](=[O:24])(=[O:25])[C:17]3[CH:16]=[CH:15][C:14]([C:11]4[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH3:3])=[CH:9][CH:10]=4)=[CH:29][C:18]=3[CH:19]=2)=[O:27])=[CH:48][CH:49]=1)[CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 219958267-[4-(2-Propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

Product 1

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-carboxamide
Yield 39.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In THF (98 ml) was dissolved 7-[4-(2-propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (4.9 g). To the mixture were added under ice-cooling thionyl chloride (1.3 ml) and DMF (3 drops), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added dropwise a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (2.93 g) and triethylamine (6.6 ml) in THF (88 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/ethanol=3/1) 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 (Compound 97) (2.9 g).

Workup

  1. additionTo the mixture were added under ice-
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate/ethanol=3/1)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7672156e53e646abb54f9c706532558c
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06235771B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes