HCID 20611467, compound → HCID 69741325, compound

HRID 1839713Notes

Reaction equation

HRID 1839713 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][C:12](=[O:18])[NH:13]3)=[CH:5][CH:4]=1.[CH3:19][N:20]([CH3:36])[C@H:21]1[CH2:25][CH2:24][N:23]([C:26]([C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][C:29]=2[CH:34]=O)=[O:27])[CH2:22]1>C(O)C.N1CCCCC1>[CH3:19][N:20]([CH3:36])[C@H:21]1[CH2:25][CH2:24][N:23]([C:26]([C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][C:29]=2[CH:34]=[C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[CH:17][C:9]=3[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:13][C:12]2=[O:18])=[O:27])[CH2:22]1

Participants

5

Reactant 2

HCID 20611467HCID 20611467, compoundHCID 225619014-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-one

Product 1

HCID 69741325HCID 69741325, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one (59.8 mg, 0.25 mmol) and 3-[(3S)-3-Dimethylamino-pyrrolidine-1-carbonyl]-5-methyl-1H-pyrrole-2-carbaldehyde (64.8 mg, 0.25 mmol) in ethanol (2 mL) was added piperidine (3 drops). The reaction mixture was stirred at room temperature for three days. A yellow solid product was precipitated out, filtered, washed by ethanol for three times, and dried under high vacuum to provide pure product 3-[3-[(3S)-3-dimethylamino-pyrrolidine-1-carbonyl)-5-methyl-1H-pyrrol-2-ylmethylene]-4-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one as a yellow solid (94 mg, 80%).

Workup

  1. customA yellow solid product was precipitated out
  2. filtrationfiltered
  3. washwashed by ethanol for three times
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-8349be28a1a348adbe6b6abf555d0194
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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