Diethyl Ether → 3-({(4-[7-(Cyclopentylamino)-2-(4methoxyphenyl)pyrazolo[1,5-alpha]pyridin-3-yl]-2-pyrimidinyl}amino)phenyl](phenyl)methanone

HRID 8503Notes

Reaction equation

HRID 8503 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[C:15]([C:16](=O)/[CH:17]=[CH:18]/N(C)C)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+]([O-])([O-])=O.[C:35]([C:43]1C=[C:45]([NH:49][C:50]([NH2:52])=[NH2+:51])[CH:46]=[CH:47][CH:48]=1)(=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:53](=O)([O-])[O-:54].[K+].[K+].CCOCC>CN(C)C=O.O>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)[C:15]([C:16]4[CH:17]=[CH:18][N:51]=[C:50]([NH:49][C:45]5[CH:46]=[CH:47][CH:48]=[CH:43][C:35]=5[C:36]5[CH:37]=[C:38]([CH:53]=[O:54])[CH:39]=[CH:40][CH:41]=5)[N:52]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 22350050(2E)-1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-oneHCID 178418771HCID 178418771, compound

Product 1

HCID 1317258883-({(4-[7-(Cyclopentylamino)-2-(4methoxyphenyl)pyrazolo[1,5-alpha]pyridin-3-yl]-2-pyrimidinyl}amino)phenyl](phenyl)methanoneYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of (2E)-1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (100 mg, 0.25 mmol) in N,N-dimethylformamide (5 mL) was added N-(3-benzoylphenyl)guanidinium nitrate (223 mg, 0.74 mmol) and potassium carbonate (102 mg, 0.74 mmol). The suspension was heated at 140 ° C. (bath temperature) for 18 hours. The mixture was cooled to room temperature, ether was added followed by water. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 to 2:1 hexanes-ethyl acetate) provided [3-({(4-[7-(Cyclopentylamino)-2-(4methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinyl}amino)phenyl](phenyl)methanone (90 mg, 76%) as a yellow solid. 1H NMR (CDCl3): δ 8.10 (d, 1 H), 8.04 (s, 1 H), 7.95 (d, 1 H), 7.81 (d, 2 H), 7.64 (d 1 H), 7.57 (d, 2 H), 7.53–7.38 (m, 6 H), 7.22 (t, 1 H), 6.98 (d, 2 H), 6.53 (d, 1 H), 6.04–5.99 (m, 2 H); 4.00 (m, 1 H), 3.86 (s,3 H), 2.12 (m, 2 H), 1.81–1.67 (m, 6 H); MS m/z581 (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 magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-fe066957bc43427db7620231eae9e5aa
Source dataset
uspto-grants-2006_08
Patent number
US07087618B2

Reaction notes

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