Diisopropylethylamine → 2-{1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl}-N-methyl-2-phenyl-acetamide

HRID 1172601Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH:7]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:6]=2[C:5]([CH3:24])=[N:4]1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:34][NH:35][C:36]([CH:38](OS(C1C=CC(C)=CC=1)(=O)=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37]>CC(C)C(C(C(C(C)C)C)=O)C>[CH2:1]([N:3]1[C:11]2[CH2:10][CH2:9][N:8]([CH:38]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:36]([NH:35][CH3:34])=[O:37])[CH:7]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=3)[C:6]=2[C:5]([CH3:24])=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

In an inert atmosphere, 1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (51 mg, 0.15 mmol) was dissolved in 3-methyl-2-butyl-ketone (MIBK) (1 ml) followed by the addition of DIPEA (21.3 mg, 0.165 mmol) and toluene-4-sulfonic acid methylcarbamoyl-phenyl-methyl ester (71.8 mg, 0.225 mmol). The reaction mixture was heated to 90° C. for 24 h, concentrated in vacuo and the crude product was purified by prep. HPLC to give 70 mg (95%) of 2-{1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl}-N-methyl-2-phenyl-acetamide. LC-MS: tR=0.84 min; [M+H]+=485.28.

Workup

concentrationconcentrated in vacuo
customthe crude product was purified by prep

Sources & evidence

ORD record: ord-1881c923c532402b97ca035a2a86e15d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834028B2

Reaction notes

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