Triethylamine → HCID 21995905, compound

HRID 1978667Notes

Reaction equation

HRID 1978667 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][CH2:18][CH2:17][C:16]([C:20]([OH:22])=O)=[CH:15][C:14]=3[CH:23]=2)=[CH:6][CH:5]=1)[CH3:2].S(Cl)(Cl)=O.[CH3:28][N:29]([CH2:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1)[CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.O>[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][CH2:18][CH2:17][C:16]([C:20]([NH:41][C:40]4[CH:42]=[CH:43][C:37]([CH2:36][N:29]([CH3:28])[CH:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[CH:38][CH:39]=4)=[O:22])=[CH:15][C:14]=3[CH:23]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 219957917-(4-Ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid

Product 1

HCID 21995905HCID 21995905, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In THF (15.3 ml) was dissolved 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid (510 mg). To the mixture were added under ice-cooling thionyl chloride (0.11 ml) and DMF (one drop), and the mixture was stirred at room temperature for 1 hour. To a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (389 mg) and triethylamine (0.87 ml) in THF (15.3 ml) was added the reaction mixture, and the mixture was stirred at room temperature for 2 hours. The reaction mixture 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) to give 7-(4-ethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzothiepine-4-carboxamide (512 mg).

Workup

  1. additionTo the mixture were added under ice-
  2. stirringthe mixture was stirred at room temperature for 2 hours
  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)

Sources & evidence

ORD record
ord-ae7121ff7f3c4d83b33ea8d7f6176a3d
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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