Water → 1-{1-[6-(5-Fluoro-2,3-dihydro-indole-1-carbonyl)-pyrazin-2-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 74666Notes

Reaction equation

HRID 74666 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.Cl[C:20]1[N:25]=[C:24]([C:26]([N:28]2[C:36]3[C:31](=[CH:32][C:33]([F:37])=[CH:34][CH:35]=3)[CH2:30][CH2:29]2)=[O:27])[CH:23]=[N:22][CH:21]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[F:37][C:33]1[CH:32]=[C:31]2[C:36](=[CH:35][CH:34]=1)[N:28]([C:26]([C:24]1[N:25]=[C:20]([N:3]3[CH2:4][CH2:5][CH:6]([N:9]4[C:17]5[C:12](=[N:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[CH2:7][CH2:8]3)[CH:21]=[N:22][CH:23]=1)=[O:27])[CH2:29][CH2:30]2

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 58386753(6-Chloropyrazin-2-yl)(5-fluoroindolin-1-yl)methanone

Product 1

HCID 583864611-{1-[6-(5-Fluoro-2,3-dihydro-indole-1-carbonyl)-pyrazin-2-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g (0.34 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one dihydrochloride, 0.11 g (0.34 mmol) (6-chloro-pyrazin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 0.20 mL (1.1 mmol) DIPEA were stirred in 1.0 mL DMF overnight at 80° C. 10 mL water were added to the reaction solution, the precipitate formed was suction filtered. The precipitate was stirred into methanol, suction filtered and dried.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-034f4e41e2fd4b04848e2ca9187c8f78
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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