Water → (R)-tert-Butyl 3-(6-(pyrazolo[1,5-a]pyridin-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate

HRID 1500762Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[F-].[Cs+].Cl[C:18]1[N:23]=[C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=23)[CH:21]=[N:20][CH:19]=1.O>CS(C)=O>[N:26]1[N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[C:24]([C:22]2[N:23]=[C:18]([NH:1][C@@H:2]3[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]3)[CH:19]=[N:20][CH:21]=2)[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Tert-Butyl (3R)-3-aminopiperidine-1-carboxylate (0.51 g, 2.54 mmol) and cesium fluoride (0.83 g, 5.46 mmol) were added to a stirred solution of 3-(6-chloropyrazin-2-yl)pyrazolo[1,5-a]pyridine (Preparation 27b, 0.42 g, 1.82 mmol) in dimethylsulfoxide (20 mL). The resulting mixture was stirred at 100° C. for 22 h before being poured onto 50 mL of water. The resultant suspension was extracted with ethyl acetate (×2) and the combined organic layers were dried over magnesium sulphate, filtered and evaporated to dryness. The crude product was purified by flash chromatography (3:7 to 7:3 ethyl acetate/hexane) to give the title compound (0.244 g, 34%) as a yellowish foam.

Workup

extractionThe resultant suspension was extracted with ethyl acetate (×2)
dry with materialthe combined organic layers were dried over magnesium sulphate
filtrationfiltered
customevaporated to dryness
customThe crude product was purified by flash chromatography (3:7 to 7:3 ethyl acetate/hexane)

Sources & evidence

ORD record: ord-9a559c2c4a994d6786fb154b77612f2f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206183B2

Reaction notes

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