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

HRID 861132Notes

Reaction equation

HRID 861132 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.C(N(CC)CC)C.[C:42](Cl)(=[O:44])[CH3:43].O>CN(C)C=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][C:42](=[O:44])[CH3:43])[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

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10297844HCID 10297844, compound

Product 1

HCID 10163732N-(3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)acetamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 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 dimethylformamide (10 mL) was added triethylamine (51 δL, 0.36 mmol). The reaction mixture was cooled to 0° C. and flushed with nitrogen, then acetyl chloride (26 μL, 0.36 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight. Water was added and the resulting mixture was extracted with ethyl acetate. The ethyl acetate phase was dried (magnesium sulfate), filtered and concentrated to a solid. This solid was purified by flash chromatography (95:5 chloroform:methanol) to give N-(3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)acetamide (151 mg, 92%) as a tan solid. 1H NMR (CDCl3): δ 8.19 (s, 1H), 7.95 (d, 1H), 7.82 (d, 1H), 7.75 (d, 1H), 7.63 (s, 1H), 7.36–7.25 (m, 3H), 6.28 (d, 1H), 6.00 (m, 2H), 5.17 (d, 1H), 4.32 (m, 1H), 3.96 (m, 1H), 2.11 (s, 3H), 2.11–2.02 (m, 4H), 1.76–1.48 (m, 12H); MS m/z 496 (M+1).

Workup

  1. customflushed with nitrogen
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate phase was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. customThis solid was purified by flash chromatography (95:5 chloroform:methanol)

Sources & evidence

ORD record
ord-022487ca7aab4db487f1ba2bfd0e48a9
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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