Carbonate Ion → HCID 178466534, 화합물

HRID 131251노트

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HRID 131251 반응식
Cl.[N:2]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.Cl.[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:40]=[CH:41][CH:42]=1)[CH2:24][N:25]1[C:29]2=[N:30][CH:31]=[N:32][C:33]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[C:28]2[CH:27]=[N:26]1)[CH3:19].ON1C2C=CC=CC=2N=N1.N=C=N.C(=O)([O-])[O-]>CN(C)C=O.C(N(CC)CC)C.C(Cl)Cl>[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:40]=[CH:41][CH:42]=1)[CH2:24][N:25]1[C:29]2=[N:30][CH:31]=[N:32][C:33]([N:34]3[CH2:35][CH2:36][N:37]([C:13]([C@H:10]4[CH2:9][CH2:8][C@H:7]([N:2]5[CH2:3][CH2:4][CH2:5][CH2:6]5)[CH2:12][CH2:11]4)=[O:15])[CH2:38][CH2:39]3)=[C:28]2[CH:27]=[N:26]1)[CH3:19]

참가 물질

9

반응물 5

HCID 19660Carbonate Ion2회HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 69298924HCID 69298924, 화합물HCID 178479759HCID 178479759, 화합물

생성물 1

HCID 178466534HCID 178466534, 화합물수율 71.5%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

To trans-4-(1-pyrrolidinyl)cyclohexanecarboxylate hydrochloride (26 mg; compound obtained in Reference example 87(2)) is added successively methylene chloride (3.5 mL), 1-(3-ethoxybenzyl)-4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride (30 mg), 0.5M 1-hydroxybenzotriazole in N,N-dimethylformamide (219 μL), triethylamine (35.6 μL) and N-cyclohexylcarbodiimide-N′-propyloxymethylpolystylene (310.4 mg, PS-Carbodiimide, 0.94 mmol/g, Argonaut Technology) and the mixture is stirred at room temperature for 24 hours by using a parallel synthesizer (Quest 210; Argonaut Technology). To the reaction mixture is added macroporous triethylammoniummethylpolystylene carbonate (120 mg, MP-Carbonate 3.04 mmol/g; Argonaut Technology) and the mixture is stirred at room temperature for 3 hours. The liquid layer is separated from the reaction mixture and the residual resin is washed successively with chloroform and methanol. The liquid layer and the washings are combined and concentrated by centrifugal concentrator. The resultant crude product is purified by HPLC (XTerra PerpMS C18 column; Waters Inc., Solvent; 10 mM ammonium carbonate:methanol=1:1→5:95) to give 1-(3-ethoxybenzyl)-4-[4-[[trans-4-(1-pyrrolidinyl)cyclohexyl]carbonyl]piperazin-1-yl]-1H-pyrazolo[3,4-d]-pyrimidine (27 mg, yield; 71%) as an amorphous powder.

후처리

  1. stirringthe mixture is stirred at room temperature for 3 hours
  2. customThe liquid layer is separated from the reaction mixture
  3. washthe residual resin is washed successively with chloroform and methanol
  4. concentrationconcentrated by centrifugal concentrator
  5. customThe resultant crude product is purified by HPLC (XTerra PerpMS C18 column; Waters Inc., Solvent; 10 mM ammonium carbonate:methanol=1:1→5:95)

출처 및 근거

ORD 기록
ord-ac73ea5c88da45dea8e1fef64b742569
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384952B2

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