HCID 10407742, compound → HCID 11740683, compound

HRID 859978Notes

Reaction equation

HRID 859978 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[OH:23])=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.ClCCl.[O-2].[O-2].[Mn+4]>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:22]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[O:23])=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 10407742HCID 10407742, compound

Product 1

HCID 11740683HCID 11740683, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (227 mg, 0.589 mmol) in chloroform (10 mL) was added manganese dioxide (454 mg, 5.22 mmol). The reaction mixture was stirred for 2 days at room temperature. The reaction mixture was diluted with dichloromethane and filtered through a pad of celite. The filtrate was concentrated to provide {3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanone (200 mg, 89%) as a white solid. Rf 0.30 (1:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.58 (d, 1H), 8.40 (d, 1H), 8.16 (d, 1H), 8.00 (d, 2H), 7.61 (t, 1H), 7.55–7.38 (m, 3H), 7.01 (t, 1H), 6.75 (d, 1H), 5.02 (d, 1H), 4.18 (m, 1H), 1.96 (m, 2H), 1.70–1.41 (m, 6H); MS m/z 384 (M+1).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2f8ece2b3cbb41828ee7bf6df282c501
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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