Water → HCID 10179118, compound

HRID 861166Notes

Reaction equation

HRID 861166 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[N-:31]=[N+]=[N-].[Na+].O.CCOCC>CN1CCCC1=O>[CH:18]1([NH:17][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)=[N:8][N:7]4[C:2]([NH2:31])=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[CH:15][N:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 57444748HCID 57444748, compound

Product 1

HCID 10179118HCID 10179118, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine (100 mg, 0.24 mmol) in 1-methyl-2-pyrrolidinone (3 mL) was added sodium azide (200 mg, 3.1 mmol). The resulting suspension was heated at 80° C. until the reaction was judged complete by thin layer chromatography. The mixture was cooled to room temperature and water and ether were added. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over sodium sulfate. Filtration and concentration followed by flash chromatography (2:1 to 1:1 hexanes-ethyl acetate) provided 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine (50 mg, 52%) as a yellow powder. 1H NMR (CDCl3): δ 8.03 (d, 1 H), 7.87 (d, 1 H), 7.62 (d, 2 H), 7.27 (m, 1 H), 7.01 (d, 2 H), 6.37 (d, 1 H), 6.17 (d, 1 H), 5.39 (s, 2 H), 5.19 (d, 1 H), 4.39 (m, 1 H), 3.90 (s, 3 H), 2.10 (m, 2 H), 1.82–1.54 (m, 6 H); MS m/z 401(M+1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-db016c4cf3cf4392b56e1fd7da22b987
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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