Trifluoroacetic acid → 4-{6-Ethoxy-5-[3-ethyl-6,7-dihydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo [4,3-d]pyrimidin-5-yl]-3-pyridylsulfonyl}-1-ethylpiperazine

HRID 1831476Notes

Reaction equation

HRID 1831476 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[CH:21]1[NH:26][C:25]2=[C:27]([CH2:37][CH3:38])[N:28]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:29]=[C:24]2[C:23](=[O:39])[NH:22]1)[CH3:2].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:6][C:5]=1[C:21]1[NH:22][C:23](=[O:39])[C:24]2[C:25](=[C:27]([CH2:37][CH3:38])[N:28]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:29]=2)[N:26]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 220522334-{6-ethoxy-5-[3-ethyl-4,5,6,7-tetrahydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridinylsulfonyl}-1-ethylpiperazine

Product 1

HCID 1355816594-{6-Ethoxy-5-[3-ethyl-6,7-dihydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo [4,3-d]pyrimidin-5-yl]-3-pyridylsulfonyl}-1-ethylpiperazineYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 4-{6-ethoxy-5-[3-ethyl-4,5,6,7-tetrahydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridinylsulfonyl}-1-ethylpiperazine (50 mg, 0.09 mmol, from step (b) above) in toluene (1 mL), was added 10% Pd/C (25 mg, 50% w/w) and trifluoroacetic acid (14 μL). The mixture was heated to 200° C. under nitrogen at 34.5 kPa (5 psi) for 6 hours. The resulting mixture was filtered and concentrated in vacuo to a pale yellow oil. This was dissolved in DCM (5 mL) and washed with NaHCO3 (2 mL), dried over MgSO4 and concentrated to give a brown oil (42 mg, 84%) as product.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo to a pale yellow oil
  3. dissolutionThis was dissolved in DCM (5 mL)
  4. washwashed with NaHCO3 (2 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-83266e8e82dc45029fcde2b132d0b295
Source dataset
uspto-grants-2006_06
Patent number
US07067660B2

Reaction notes

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