Diisopropyl Ether → HCID 67541275, compound

HRID 1027074Notes

Reaction equation

HRID 1027074 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:25]([N:27]1[CH2:32][CH2:31][C:30]2([C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]([CH3:41])=[CH:33]2)[CH2:29][CH2:28]1)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(C)C)(C)C>C(O)C.[C].[Pd]>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:25]([N:27]1[CH2:28][CH2:29][C:30]2([C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]([CH3:41])[CH2:33]2)[CH2:31][CH2:32]1)=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7914Diisopropyl EtherHCID 67540114HCID 67540114, compound

Product 1

HCID 67541275HCID 67541275, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

N-[7-Benzylamino-6-(3-methylspiro[inden-1,4′-piperidine]-1′-ylcarbonyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]methanesulfonamide (0.035 g, 0.061 mmol) obtained in Example 111, step 3 was dissolved in ethanol (2.0 ml), 10% palladium-carbon (0.079 g, 0.382 mmol) was added, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was filtered through celite and washed with chloroform, and the filtrate was concentrated under reduced pressure to give a residue. Diisopropyl ether was added to the residue and the precipitated crystals were collected by filtration to give the title compound (0.011 g, 32%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with chloroform
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a residue
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a4f06e8e120c4040b5de49e04ffc96ac
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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