HCID 68519649, compound → HCID 68515091, compound

HRID 1171025Notes

Reaction equation

HRID 1171025 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH3:21])[CH:12]=3)[N:9]=[C:8]([C:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH:27]=3)[C:4]=2[N:5]=[CH:6][N:7]=1>[Pd].CO>[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:20][CH3:21])[CH:12]=3)[N:9]=[C:8]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 68519649HCID 68519649, compound

Product 1

HCID 68515091HCID 68515091, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-[7-amino-1-(3-methoxy-4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate (200 mg, 0.428 mmol) and 10% palladium on carbon (100 mg) in methanol (20 mL) and hydrogenated in a Parr shaker at 55 psi for 18 hours. The catalyst was removed by filtration through a pad of diatomaceous earth and the filtrate concentrated under reduced pressure then the residue was dissolved methanol (20 mL). Platinum (IV) oxide (100 mg) was added and the mixture was hydrogenated in a Parr shaker at 55 psi for 30 hours. The catalyst was removed by filtration through a pad of diatomaceous earth and the filtrate concentrated under reduced pressure to provide the title compound as a brown solid (175 mg, 93%): 1H NMR (DMSO-d6, 400 MHz) δ 8.22 (s, 1H), 6.96 (d, 1H), 6.84 (d, 1H), 6.74 (d, 1H), 6.5 (bs, 2H), 5.75 (bs, 2H), 4.03 (m, 2H), 3.76 (s, 3H), 3.22 (m, 1H), 2.93 (m, 2H), 1.7-2.1 (m, 4H), 1.42 (s, 9H) RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 16.93 min; MS: MH+ 440.2

Workup

  1. customThe catalyst was removed by filtration through a pad of diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutionthe residue was dissolved methanol (20 mL)
  4. additionPlatinum (IV) oxide (100 mg) was added
  5. waitthe mixture was hydrogenated in a Parr shaker at 55 psi for 30 hours
  6. customThe catalyst was removed by filtration through a pad of diatomaceous earth
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a41d6d246c34ebb995b648fdd9b4bd1
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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