HCID 9911644, compound → HCID 9804154, compound

HRID 396381Notes

Reaction equation

HRID 396381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)[C:10]3[C:11]([N:22]=2)=[N:12][C:13]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1>CC(O)=O.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)[C:10]3[C:11]([N:22]=2)=[N:12][C:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 9911644HCID 9911644, compound

Product 1

HCID 9804154HCID 9804154, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(4-pyridinyl)imidazo[4,5-b]pyridine (example 7; 100 mg; 0.22 mmol) is dissolved in HOAc (120 ml) and hydrogenated over Pd/C (10%, 200 mg) in a Parr apparatus for 48 h at room temperature. The reaction mixture is filtered and evaporated to dryness delivering the title compound as yellow crystals, which are recrystallised from MeOH and gave the title compound as colorless crystals (70 mg; 65%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated to dryness
  3. customare recrystallised from MeOH

Sources & evidence

ORD record
ord-4bdee361a71643088d4d85a2f44a74f4
Source dataset
uspto-grants-2003_08
Patent number
US06608072B1

Reaction notes

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