Water → HCID 71549931, compound

HRID 628465Notes

Reaction equation

HRID 628465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=3)=[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.O.[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH:33]1([C:36]([N:23]([C:19]2[CH:18]=[C:17]([C:16]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[N:9][N:10]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=34)[CH:22]=[CH:21][N:20]=2)[C:44]([CH:43]2[CH2:41][CH2:42]2)=[O:40])=[O:37])[CH2:35][CH2:34]1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 67438844HCID 67438844, compound

Product 1

HCID 71549931HCID 71549931, compoundYield 75%

Procedure

154 mg (0.5 mmol) of 4-[2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl]pyridin-2-amine and 193 mg (1.5 mmol, 3 eq) of Huenigs base are dissolved in 4 mL tetrahydrofuran. To this are added 156 mg of cyclopropanecarbonyl chloride (1.5 mmol, 3 eq) and the reaction mixture is stirred for 20 hrs at room temperature. Then the reaction mixture is treated with water and extracted with ethyl acetate. The organic phases are dried over Na2SO4 and the solvents are removed under vacuum. The crude material is purified by column chromatography on silica (eluent cyclohexane/ethyl acetate). 180 mg (75%) of N-(cyclopropylcarbonyl)-N-{4-[2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl]pyridin-2-yl}cyclopropanecarboxamide are obtained as a colourless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phases are dried over Na2SO4
  3. customthe solvents are removed under vacuum
  4. customThe crude material is purified by column chromatography on silica (eluent cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-1e9fc49386dd4861a763efe5cca6d08b
Source dataset
uspto-grants-2016_04
Patent number
US09314026B2

Reaction notes

Loading…