Potassium Carbonate → HCID 71515487, compound

HRID 1466214Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:26]([CH3:27])=[N:25][N:24]([CH3:28])[C:12]2=[N:13][C:14]=1[N:15]([CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH2:16][CH:17]1[CH2:19][CH2:18]1.Cl[C:39]1[N:44]=[CH:43][C:42]([C:45](=[O:47])[CH3:46])=[CH:41][N:40]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:17]1([CH2:16][N:15]([CH2:20][CH:21]2[CH2:23][CH2:22]2)[C:14]2[N:13]=[C:12]3[N:24]([CH3:28])[N:25]=[C:26]([CH3:27])[C:11]3=[CH:10][C:9]=2[CH2:8][N:7]([CH2:6][C:5]2[CH:29]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:31]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:4]=2)[C:39]2[N:44]=[CH:43][C:42]([C:45](=[O:47])[CH3:46])=[CH:41][N:40]=2)[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 65 °C

Procedure

5-(((3,5-bis(trifluoromethyl)benzyl)amino)methyl)-N,N-bis(cyclopropylmethyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-amine (0.761 mmol, 0.400 g) in DMF was treated with 1-(2-chloropyrimidin-5-yl)ethanone (0.761 mmol, 0.119 g) and K2CO3 (2.283 mmol, 0.315 g). The reaction mixture was stirred at 60-70° C. for 12-16 h. The reaction mixture was then extracted with EtOAc. The combined organic layer was washed with water and brine solution, dried over sodium sulphate, concentrated under reduced pressure and purified by column chromatography using silica gel and 50% EtOAc in petroleum ether as eluent to get the title compound.

Workup

extractionThe reaction mixture was then extracted with EtOAc
washThe combined organic layer was washed with water and brine solution
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
custompurified by column chromatography

Sources & evidence

ORD record: ord-d53933d784e443bfad8d35c5125edda2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000007B2

Reaction notes

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