Fusaric Acid → (5-Butyl-pyridin-2-yl)-{4-[1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

HRID 719463

반응식

HRID 719463 반응식
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC(OC(C)C)=O.Cl.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36]3=[N:37][CH:38]=[N:39][C:40]([O:41][CH:42]4[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]4)=[C:35]3[CH:34]=[N:33]2)=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(N(CC)CC)C>CN(C=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([N:45]2[CH2:46][CH2:47][CH:42]([O:41][C:40]3[N:39]=[CH:38][N:37]=[C:36]4[N:32]([C:29]5[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:24])=[O:25])=[CH:31][CH:30]=5)[N:33]=[CH:34][C:35]=34)[CH2:43][CH2:44]2)=[O:13])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 3442Fusaric AcidHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 218977741-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

생성물 1

HCID 21897785(5-Butyl-pyridin-2-yl)-{4-[1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone수율 14.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Butyl-pyridine-2-carboxylic acid (92 mg, 0.51 mmol) and isopropyl chloroformate (70 μL, 0.51 mmol) were dissolved in DMF and stirred at room temperature for 40 min. 1-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (70 mg, 0.17 mmol) and triethylamine (72 μL, 0.51 mmol) were added next and continued to stir for 24 hours. Progress of the reaction was monitored by TLC and LCMS. Removal of organic solvents in vacuo and purification by HPLC afforded Compound A125 as a white solid (13 mg, 13%). Exact mass calculated for C27H30N6O4S 534.63, found 535.20 (MH+).

후처리

  1. stirringto stir for 24 hours
  2. customRemoval of organic solvents
  3. customin vacuo and purification by HPLC

출처 및 근거

ORD 기록
ord-9944c216294d426aa0aa521f149a665f
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132426B2

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