Water → methanesulfonic acid 2-methyl-3-[4-(7-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrazolo[1,5-a]pyridin-5-ylmethyl ester

HRID 402872노트

반응식

HRID 402872 반응식
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].O[CH2:11][C:12]1[CH:17]=[CH:16][N:15]2[N:18]=[C:19]([CH3:38])[C:20]([C:21]3[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=3[C:26]3[C:34]4[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=4)[NH:28][CH:27]=3)=[C:14]2[CH:13]=1.C(N(CC)CC)C.O>C1COCC1>[CH3:38][C:19]1[C:20]([C:21]2[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=2[C:26]2[C:34]3[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[C:14]2[CH:13]=[C:12]([CH2:11][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=[CH:16][N:15]2[N:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 591920083-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

생성물 1

HCID 59192039methanesulfonic acid 2-methyl-3-[4-(7-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrazolo[1,5-a]pyridin-5-ylmethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methanesulfonic anhydride (815 mg, 4.49 mmol, 4.3 equiv) is added at room temperature under an atmosphere of argon to a solution of 3-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (400 mg, 1.04 mmol) and of triethyl amine (0.314 ml, 2.25 mmol, 2.2 equiv) in anhydrous THF (10 ml). The reaction mixture is stirred for 1 hour at room temperature. Water is added, and the mixture is extracted three times with EtOAc. The combined organic layers are dried over Na2SO4, filtered, and concentrated in vacuo. The residue (450 mg, 94%) is used directly in the next transformation.

후처리

  1. extractionthe mixture is extracted three times with EtOAc
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3ef7ad30ec84484eac45b30dea08e87d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742132B2

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