Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate

HRID 1036633노트

반응식

HRID 1036633 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:28][CH:29]=O)[CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH:28]=[CH:29][C:15]3[N:14]([C:18]4[N:19]=[CH:20][CH:21]=[CH:22][C:17]=4[C:16]=3[CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86655915Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

생성물 1

HCID 86655916methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate수율 70.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (0.69 g, 1.6 mmol) in toluene (50 mL) was added PPTS (0.41 g, 1.6 mmol, 1.2 equiv.). After a period of 10 h at 90° C., the reaction mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate) to give 469 mg of the title compound.

후처리

  1. customthe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-e39ee06a536a4ac7a2e2f9cf3dfeb2c7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546422B2

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