Cyclopropanecarbonyl chloride → N'-(Cyclopropylcarbonyl)-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490886Notes

Reaction equation

HRID 490886 reaction equation
Cl.Cl.[CH2:3]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:21]([NH:23][NH2:24])=[O:22])[C:13]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]2[CH:7]=[N:6]1)[CH3:4].CCN(C(C)C)C(C)C.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1>C1COCC1>[CH:34]1([C:37]([NH:24][NH:23][C:21]([C:12]2[C:13]([NH:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[C:8]3[CH:7]=[N:6][N:5]([CH2:3][CH3:4])[C:9]3=[N:10][CH:11]=2)=[O:22])=[O:38])[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 534878281-Ethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide dihydrochloride

Product 1

HCID 57675148N'-(Cyclopropylcarbonyl)-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazideYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 19 (0.045 g) in THF (2 ml) was treated with DIPEA (0.045 ml), then with cyclopropylcarbonyl chloride (0.013 g) and stirred at room temperature for 16 h. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The layers were separated and the organic layer concentrated in vacuo, then applied to an SPE cartridge (aminopropyl, 1 g). The column was eluted with methanol to afford Intermediate 20 as a white solid (0.02 g). LCMS showed MH+=373; TRET=2.15 min.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. customThe layers were separated
  4. concentrationthe organic layer concentrated in vacuo
  5. washThe column was eluted with methanol

Sources & evidence

ORD record
ord-5644c95b75ba4d8da6d565b0e8131feb
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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