Pyridine → N-(3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)methanesulfonamide

HRID 861133Notes

Reaction equation

HRID 861133 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([NH:16][CH:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C(OCC)(=O)C>CN(C)C=O.O>[CH:17]1([NH:16][C:15]2[N:10]3[N:9]=[C:8]([C:4]4[CH:3]=[C:2]([NH:1][S:42]([CH3:41])(=[O:44])=[O:43])[CH:7]=[CH:6][CH:5]=4)[C:22]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:31][CH2:32][CH2:33][CH2:34]5)[N:24]=4)=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 10297844HCID 10297844, compound

Product 1

HCID 10302061N-(3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)methanesulfonamideYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-(3-aminophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (150, mg, 0.33 mmol) in N,N-dimethylformamide (5 mL) was added pyridine (40 μL, 0.49 mmol). The reaction mixture was cooled to 0° C. under nitrogen, then methanesulfonyl chloride (28 μL, 0.36 mmol) was added dropwise. After stirring at room temperature for 18 hours, the reaction mixture turned clear. Ethyl acetate and water were added and the phases separated. The organic phase was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (95:5 chloroform:methanol) gave N-(3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)methanesulfonamide (170 mg, 96%) as a yellow syrup. 1H NMR (CDCl3): δ 7.93 (d, 1H), 7.66 (d, 1H), 7.42 (m, 1H), 7.35–7.25 (m, 5H), 6.25 (m, 1H), 5.99 (m, 2H), 5.62 (broad, 1H), 4.29 (m, 1H), 3.96 (m, 1H), 2.94 (s, 3H), 2.10–1.99 (m, 4H), 1.77–1.49 (m, 12H). MS m/z 532 (M+1).

Workup

  1. customthe phases separated
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-f9c259688f8c46d49a2e2ad0a09aea97
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

Loading…