Cyclopentylamine → HCID 10042600, compound

HRID 859971Notes

Reaction equation

[CH2:1]([C:5]1[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16](S(C)=O)[N:15]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)[CH:2]([CH3:4])[CH3:3].[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH:23]1([NH:28][C:16]2[N:15]=[C:14]([C:13]3[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[N:6][N:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=34)[CH:19]=[CH:18][N:17]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 9995778HCID 9995778, compound

Product 1

HCID 10042600HCID 10042600, compoundYield 89%

Procedure

A solution of 2-isobutyl-3-[2-(methylsulfinyl)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine (930 mg, 2.98 mmol) in cyclopentylamine (5 mL) was heated at 130° C. for 4 h. The mixture was cooled to room temperature and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (2:1 to 1:1 hexane-ethyl acetate) to give N-cyclopentyl-4-(2-isobutylpyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (890 mg, 89%) as a White solid. 1H NMR (CDCl3) δ 8.44 (d, 1H), 8.28–8.25 (m, 2H), 7.26 (m, 1H), 6.85–6.76 (m, 2H), 5.08 (m, 1H), 4.40 (m, 1H), 3.00 (d, 2H), 2.26–2.05 (m, 3H), 1.83–1.51 (m, 6H), 1.00 (d, 6H); MS m/z 336 (M+1).

Workup

concentrationconcentrated in vacuo
customthe residue was purified by flash chromatography on silica gel (2:1 to 1:1 hexane-ethyl acetate)

Sources & evidence

ORD record: ord-1390de27ea17497383964a069ac18f05
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153863B2

Reaction notes

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