Diethyl Ether → 3-[2-(Cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 1373799Notes

Reaction equation

HRID 1373799 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[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-:30]=[N+]=[N-].[Na+].CCOCC>CN(C)C=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]([F:29])=[CH:27][CH:28]=4)=[N:8][N:7]4[C:2]([NH2:30])=[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

5

Reactant 3

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 102728224-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

Product 1

HCID 52756893-[2-(Cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (53 mg, 0.13 mmol) in N,N-dimethylformamide (4 mL) was added sodium azide (85 mg, 1.3 mmol). The resultant mixture was heated to 100° C. for 18 hours. The reaction mixture was cooled to room temperature and ether was added. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 to 1:1 hexanes:ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (30 mg, 60%) as an oil. 1H NMR (CDCl3) δ 7.97 (d, 1H), 7.77 (d, 1H), 7.60 (m, 2H), 7.22 (m, 1H), 7.10 (t, 2H), 6.26 (d, 1H), 6.14 (d, 1H), 5.26 (s, 2H), 5.09 (d, 1H), 4.29 (m, 1H), 2.06–1.99 (m, 2H), 1.75–1.45 (m, 6H); MS m/z 389 (M+1). This material was taken up in ether and treated with hydrochloric acid in ether to yield a yellow precipitate which was isolated by filtration as a hydrochloride salt.

Workup

  1. washThe organic layer was washed with brine
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialthe combined organics dried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-acbe079b83a448b985a6f2a361e10a4d
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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