Pyridinium chloride → 4'-(5-fluoro-2,3-dihydroindole-1-carbonyl)-4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H,1'H-[1,2']bipyridinyl-6'-one

HRID 2059983Notes

Reaction equation

HRID 2059983 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:18]=[C:17]([O:19]C)[N:16]=[C:15]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[NH:29][C:28]4=[O:36])[CH2:23][CH2:22]3)[CH:14]=1)=[O:12])[CH2:6][CH2:5]2.Cl.N1C=CC=CC=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[NH:29][C:28]4=[O:36])[CH2:23][CH2:22]3)[NH:16][C:17](=[O:19])[CH:18]=1)=[O:12])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 583865221-[4'-(5-fluoro-2,3-dihydroindole-1-carbonyl)-6'-methoxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydroimidazo[4,5-b]pyridin-2-one

Product 1

HCID 426133804'-(5-fluoro-2,3-dihydroindole-1-carbonyl)-4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H,1'H-[1,2']bipyridinyl-6'-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A well stirred mixture of 20 mg (0.041 mmol) 1-[4′-(5-fluoro-2,3-dihydroindole-1-carbonyl)-6′-methoxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-1,3-dihydroimidazo[4,5-b]pyridin-2-one and 100 mg (0.865 mmol) pyridine hydrochloride was kept in a melt for 7 min using a hot air blower. After the reaction mixture had cooled it was dissolved in DMF and purified by preparative HPLC. The fractions containing the product were combined and lyophilised.

Workup

  1. temperatureAfter the reaction mixture had cooled it
  2. custompurified by preparative HPLC
  3. additionThe fractions containing the product

Sources & evidence

ORD record
ord-9e4d5010c7d94f63ac8e4b88aa01b0c7
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

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