Water → N-pyrazolo[1,5-a]pyridin-3-ylcyclopropanecarboxamide

HRID 859134Notes

Reaction equation

HRID 859134 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.C(N(CC)CC)C.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.O>CCOC(C)=O.C([O-])(O)=O.[Na+]>[N:4]1[N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=[C:2]([NH:1][C:21]([CH:18]2[CH2:20][CH2:19]2)=[O:22])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 12068469Pyrazolo[1,5-a]pyridin-3-amine

Product 1

HCID 69588964N-pyrazolo[1,5-a]pyridin-3-ylcyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-aminopyrazolo[1,5-a]pyridine (0.74 g, 5.55 mmol) and triethylamine (1.0 ml, 6.95 mmol) in EtOAc (15.0 mL) was added cyclopropanecarbonyl chloride (0.63 mL, 6.95 mmol). The resulting mixture was stirred at room temperature for 48 h and diluted with saturated NaHCO3 solution. More EtOAc and H2O were added and separated. The EtOAc solution was concentrated in vacuo to dryness. The residue was recrystalized from EtOAc to give 0.86 g (77%) of light brown solid as the title compound: mp 159–162° C.; IR (diffuse reflectance) 3207, 3085, 3073, 3044, 2998, 1645, 1596, 1477, 1401, 1356, 1330, 1218, 950, 738, 727 cm−1; MS (EI) m/z 201 (M+); Anal. Calcd for C11H11N3O: C, 65.66; H, 5.51; N, 20.88. Found: C, 65.52; H, 5.48; N, 20.82.

Workup

  1. customseparated
  2. concentrationThe EtOAc solution was concentrated in vacuo to dryness
  3. customThe residue was recrystalized from EtOAc

Sources & evidence

ORD record
ord-4bda1ea074f643c9a8635c2d2fcdf148
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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