Cesium carbonate → HCID 67499459, compound

HRID 1484734Notes

Reaction equation

I[C:2]1[C:3]([CH3:13])=[N:4][N:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=1.[N:14]1[C:23]2[CH:22]([C:24](=O)C)CCCC=2C=CC=1.C1(N)CC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.[Cu]Br>[CH:23]1([NH:14][C:2]2[C:3]([CH3:13])=[N:4][N:5]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=2)[CH2:22][CH2:24]1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 3-(4-iodo-3-methyl-1H-pyrazol-1-yl)pyridine (2.0 g, 7.02 mmol) in dimethylsulfoxide (7.02 ml) was added 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone (0.246 g, 1.403 mmol), cyclopropanamine (0.486 ml, 7.02 mmol), cesium carbonate (6.86 g, 21.05 mmol) and copper(I) bromide (0.101 g, 0.702 mmol). The reaction mixture was stirred at 35° C. for 2 days. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organics were washed with brine, concentrated and chromatographed (0-100% ethyl acetate/hexanes) to give N-cyclopropyl-3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (269 mg, 1.255 mmol, 17.90%) as a yellow solid: mp 104.0-107.0° C.; 1H NMR (400 MHz, CDCl3) δ 8.89 (dd, J=2.7, 0.5 Hz, 1H), 8.41 (dd, J=4.7, 1.4 Hz, 1H), 7.96 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.51 (s, 1H), 7.33 (ddd, J=8.3, 4.7, 0.7 Hz, 1H), 3.42 (s, 1H), 2.53-2.42 (m, 1H), 2.22 (s, 3H), 0.72-0.65 (m, 2H), 0.60-0.53 (m, 2H); ESIMS m/z 215 ([M+H]+).

Workup

extractionextracted with dichloromethane
washThe combined organics were washed with brine
concentrationconcentrated
customchromatographed (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-03561dcf064746ecb20dcd9215875c20
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422278B2

Reaction notes

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