Piperidine → HCID 59250078, compound

HRID 2191511Notes

Reaction equation

HRID 2191511 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=[O:20])[N:8]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][C:3]=1[CH:21]=O.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[CH2:31][S:32]([C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][C:39](=[O:44])[CH2:38]2)(=[O:34])=[O:33].N1CCCCC1>C(O)C>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[CH2:31][S:32]([C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][C:39](=[O:44])/[C:38]/2=[CH:21]\[C:3]1[NH:4][C:5]2[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:7](=[O:20])[C:6]=2[C:2]=1[CH3:1])(=[O:33])=[O:34].[CH3:1][C:2]1[C:6]2[C:7](=[O:20])[N:8]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 181797685-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-oneHCID 592500683-Methyl-5-(2-morpholin-4-yl-ethyl)-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 2

HCID 25130953HCID 25130953, compoundHCID 59250078HCID 59250078, compoundYield 368.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methyl-5-(2-morpholin-4-yl-ethyl)-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 10c (100 mg, 0.325 mmol) and 5-(2,6-dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one 64c (104 mg, 0.293 mmol) were dissolved in 3 ml of ethanol, and added with 52 μl of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was heated to reflux for 2 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and filtered. The filter cake was washed with anhydrous ethanol (3 ml×2) and dried to obtain the title compound (Z)-2-(5-(2,6-dichlorobenzylsulfonyl)-2-oxoindolin-3-yl idene)methyl)-3-methyl-5-(2-morpholinoethyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 64 (166 mg, yield 88%) as an orange solid.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. filtrationfiltered
  5. washThe filter cake was washed with anhydrous ethanol (3 ml×2)
  6. customdried

Sources & evidence

ORD record
ord-673cc8ee1a704cc5b39f807ee4bed420
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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