HCID 10140601, compound → HCID 10134921, compound

HRID 456718Notes

Reaction equation

HRID 456718 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:15]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[N:26]=3)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH:32]1([NH:31][C:27]2[N:26]=[C:25]([C:15]3[N:11]4[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]4=[N:17][C:16]=3[C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH:30]=[CH:29][N:28]=2)[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 10140601HCID 10140601, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 10134921HCID 10134921, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 4-[8-(benzyloxy)-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine (30 mg, 0.063 mmol) in ethanol (2 mL) was added 10% palladium on carbon (4 mg). The mixture was stirred under 10 psi of hydrogen for 3 hours. Additional 10% palladium on carbon (5 mg) was added and the mixture stirred under 15 psi of hydrogen for 1 hour. The catalyst was removed by filtering the mixture through Celite. The filtrate was concentrated and the residue purified by silica chromatography, eluting with 10% acetone in dichloromethane to yield 15 mg (60%) of 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-ol. 1H NMR (CDCl3): δ 9.10 (m, 1H), 8.13 (d, 1H), 7.64 (dd, 2H), 7.15 (t, 2H), 6.86 (m, 2H), 6.41 (d, 1H), 5.27 (d, 1H), 4.38 (m, 1H), 2.13 (m, 2H), 1.73 (m, 6H); MS m/z 390 (M+1).

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering the mixture through Celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by silica chromatography
  5. washeluting with 10% acetone in dichloromethane

Sources & evidence

ORD record
ord-9e7735316a0041f59a3fb634a876d11a
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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