Acetic Acid → 1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

HRID 1172600Notes

Reaction equation

HRID 1172600 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][C:5]([CH3:11])=[N:4]1)[CH3:2].C(O)(=O)C.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH:26]=O)=[CH:20][CH:19]=1>C(O)C>[CH2:1]([N:3]1[C:7]2[CH2:8][CH2:9][NH:10][CH:26]([CH2:25][CH2:24][C:21]3[CH:22]=[CH:23][C:18]([C:17]([F:16])([F:28])[F:29])=[CH:19][CH:20]=3)[C:6]=2[C:5]([CH3:11])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 216838073-[4-(Trifluoromethyl)phenyl]propanalHCID 451214772-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethylamine

Product 1

HCID 668828441-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridineYield 34.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethylamine (148 mg, 0.97 mmol) was dissolved in ethanol (3 ml) and acetic acid (116.5 mg. 1.94 mmol) was added followed by the addition of 3-(4-trifluoromethyl-phenyl)-propionaldehyde (197 mg, 0.97 mmol). The mixture was sealed and put in the microwave oven (100 Watts; 130° C., 14 bar, 6 minutes). The solvents were removed under reduced pressure and the residue was purified by prep. HPLC to give 113 mg (34.5%) of 1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine. LC-MS: tR=0.75 min; [M+H]+=338.22.

Workup

  1. customThe mixture was sealed
  2. customput in the microwave oven (100 Watts; 130° C., 14 bar, 6 minutes)
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was purified by prep

Sources & evidence

ORD record
ord-3c747d71a7374d06a5219a44b423ece6
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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