Piperidine → HCID 25130954, compound

HRID 2191512Notes

Reaction equation

HRID 2191512 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=[O:19])[N:8]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][C:3]=1[CH:20]=O.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][S:30]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][C:37](=[O:42])[CH2:36]3)(=[O:32])=[O:31])=[CH:25][CH:24]=1.N1CCCCC1>C(O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][S:30]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][C:37](=[O:42])[C:36]3=[CH:20][C:3]2[NH:4][C:5]3[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:7](=[O:19])[C:6]=3[C:2]=2[CH3:1])(=[O:32])=[O:31])=[CH:27][CH:28]=1.[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][S:30]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][C:37](=[O:42])/[C:36]/3=[CH:20]\[C:3]2[NH:4][C:5]3[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:7](=[O:19])[C:6]=3[C:2]=2[CH3:1])(=[O:32])=[O:31])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 18179638HCID 18179638, compoundHCID 592500963-Methyl-4-oxo-5-(2-pyrrolidin-1-yl-ethyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 2

HCID 25130954HCID 25130954, compoundYield 164.3%HCID 68527884HCID 68527884, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methyl-4-oxo-5-(2-pyrrol 8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 28c (60.2 mg, 0.21 mmol) and 5-(4-fluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one 65a (57.6 mg, 0.19 mmol) were dissolved in 2 ml of ethanol, and added with 50 μl of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was heated to reflux for 3 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-(4-fluoro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-5-(2-pyrrolidin-1-yl-ethyl)-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 65 (90 mg, yield 81.8%) as an orange solid.

Workup

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

Sources & evidence

ORD record
ord-d79f583c589647298398631a8a3d5dff
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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