(2S)-2-methylpyrrolidine → (S)-4-(4-(difluoromethyl)thiazol-2-yl)-1-methyl-N-(2-(2-methylpyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide

HRID 60139Notes

Reaction equation

HRID 60139 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.Br[C:8]1[N:33]=[C:11]2[CH:12]=[C:13]([NH:16][C:17]([C:19]3[N:23]([CH3:24])[N:22]=[CH:21][C:20]=3[C:25]3[S:26][CH:27]=[C:28]([CH:30]([F:32])[F:31])[N:29]=3)=[O:18])[CH:14]=[CH:15][N:10]2[N:9]=1>C(OCC)(=O)C>[F:32][CH:30]([F:31])[C:28]1[N:29]=[C:25]([C:20]2[CH:21]=[N:22][N:23]([CH3:24])[C:19]=2[C:17]([NH:16][C:13]2[CH:14]=[CH:15][N:10]3[N:9]=[C:8]([N:3]4[CH2:4][CH2:5][CH2:6][C@@H:2]4[CH3:1])[N:33]=[C:11]3[CH:12]=2)=[O:18])[S:26][CH:27]=1

Participants

4

Reactant 2

HCID 6999702(2S)-2-methylpyrrolidineHCID 117776784N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-4-(4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxamide

Product 1

HCID 90383119(S)-4-(4-(difluoromethyl)thiazol-2-yl)-1-methyl-N-(2-(2-methylpyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

An (S)-2-methylpyrrolidine (0.5 ml) solution of the N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-4-(4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxamide (30 mg) synthesized in (Example 3.15) <Step 6> was stirred under microwave heating at 150° C. for 1 hour. Thereafter, ethyl acetate (20 ml) was added to the reaction solution, and the mixed solution was successively washed with water (15 ml) twice and with a saturated saline (10 ml) once, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=40:60), so as to obtain the title compound (13 mg) in the form of a light yellow solid.

Workup

  1. washthe mixed solution was successively washed with water (15 ml) twice
  2. dry with materialwith a saturated saline (10 ml) once, and was then dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=40:60)

Sources & evidence

ORD record
ord-b1960930ea2f42619978346ebfd67a5e
Source dataset
uspto-grants-2016_09
Patent number
US09440970B2

Reaction notes

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