4-(3-Piperidin-1-yl-propionyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde → 4-(2,6-Difluoro-phenyl)-3-[1-[4-(3-piperidin-1-yl-propionyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepin-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1839814Notes

Reaction equation

HRID 1839814 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[NH:18][C:19]([CH:21]=O)=[CH:20][C:12]2=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1[CH2:33][C:34](=[O:40])[NH:35]2>N1CCCCC1.C(O)C>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1/[C:33](=[CH:21]/[C:19]1[NH:18][C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][N:11]([C:9](=[O:10])[CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[C:12]=3[CH:20]=1)/[C:34](=[O:40])[NH:35]2

Participants

5

Reactant 2

HCID 225616984-(3-Piperidin-1-yl-propionyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehydeHCID 225617464-(2,6-Difluoro-phenyl)-1,3-dihydro-indol-2-one

Product 1

HCID 600612814-(2,6-Difluoro-phenyl)-3-[1-[4-(3-piperidin-1-yl-propionyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepin-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 60.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

4-(3-Piperidin-1-yl-propionyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde (80 mg, 0.26 mmol) was condensed with 4-(2,6-difluoro-phenyl)-1,3-dihydro-indol-2-one (61 mg, 0.25 mmol) and piperidine (1 drop) in ethanol (3 mL) at rt for over the weekend. The precipitate was filtered, washed with ethanol and dried to give 80 mg of the titled compound as a yellow solid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-2667cd709f224fc8b4fa69b148d196c3
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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