Dodecanoyl chloride → 4-(3-Chloro-phenylamino)-3-(4-[n-dodecanoyl]-piperazin-1-yl)-1h-pyrazolo[3,4-d]pyrimidine

HRID 1068896Notes

Reaction equation

HRID 1068896 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]3[NH:17][N:18]=[C:19]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:12]=23)[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[C:32](Cl)(=[O:44])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>O.O1CCOCC1>[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]3[NH:17][N:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([C:32](=[O:44])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:22][CH2:21]4)[C:12]=23)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 11430Potassium CarbonateHCID 211906574-(3-chlorophenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride

Product 1

HCID 211907004-(3-Chloro-phenylamino)-3-(4-[n-dodecanoyl]-piperazin-1-yl)-1h-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Analogously to Example 26, 100 mg (0.248 mmol) of 4-(3-chloro-phenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrmidine dihydrochloride and 103 mg (0.74 mmol) of potassium carbonate in 10 ml of water are reacted with 81.5 mg (0.37 mmol) of lauric acid chloride in 10 ml of dioxane and extracted. Column chromatography (SiO2; methylene chloride/ethyl acetate/acetic acid=50:50:1) yields 4-(3-chloro-phenylamino)-3-(4-[n-dodecanoyl]-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=22.6; FAB-MS: (M+H)+=512.

Workup

  1. extractionextracted

Sources & evidence

ORD record
ord-d7046b47f4a44631bb7d0d5ecd5bbe49
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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