Methanol → HCID 59408756, compound

HRID 1188145Notes

Reaction equation

HRID 1188145 reaction equation
CO.[N+:3]([C:6]1[N:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[N:9]=[C:8]([C:17]([NH:19][C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[N:22]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[N:21]=2)=[O:18])[CH:7]=1)([O-])=O>C1COCC1.[Pd]>[NH2:3][C:6]1[N:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[N:9]=[C:8]([C:17]([NH:19][C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[N:22]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[N:21]=2)=[O:18])[CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 59408739HCID 59408739, compound

Product 1

HCID 59408756HCID 59408756, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methanol (5 mL) and Pd/C were added to a solution of 5-nitro-1-(tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-1H-pyrazole-3-carboxamide (183 mg, 0.38 mmol) in THF. The flask was then evacuated and filled with hydrogen. The reaction mixture was stirred for 16 hrs. The catalyst was filtered on celite and the solution was concentrated and dried to give 5-amino-1-(tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-1H-pyrazole-3-carboxamide (170 mg, quantitative).

Workup

  1. customThe flask was then evacuated
  2. additionfilled with hydrogen
  3. filtrationThe catalyst was filtered on celite
  4. concentrationthe solution was concentrated
  5. customdried

Sources & evidence

ORD record
ord-a7882c9f84c141dc9728664ebfdde183
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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