Ethyl Acetate → N-(3-(3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide

HRID 531481노트

반응식

HRID 531481 반응식
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:22]=[N:23][N:24]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=5)[CH:25]=4)=[CH:19][N:18](C(OC(C)(C)C)=O)[C:15]3=[N:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].O1CCOCC1.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.CCCCCC>[N+:33]([C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][N:24]1[CH:25]=[C:21]([C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([C:8]4[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[CH:10][CH:9]=4)[CH:13]=3)[NH:18][CH:19]=2)[CH:22]=[N:23]1)([O-:35])=[O:34]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 118523971tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

생성물 1

HCID 72944751N-(3-(3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide수율 62%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8058Hexane용매

실험 절차

tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (200 mg, 0.409 mmol) dissolved in 10 ml of methanol and added 1,4-dioxane/HCl (2 ml) at 0° C. and stirred at room temperature for 15 h. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was concentrated under reduced pressure to afford crude product. The residue was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2×25 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 100 mg (62% yield) of the pure required product. 1H NMR (DMSO-d6, 400 MHz): δ11.82 (s, 1H), 9.85 (s, 1H), 8.47 (s, 2H), 8.33 (s, 1H), 8.18-8.15 (d, 2H), 8.00 (s, 1H), 7.806-7.7.800 (d, 1H), 7.75-7.34 (d, 1H), 7.69-7.65 (t, 1H), 7.52-7.44 (m, 3H), 7.24-7.22 (d, 1H), 5.55 (s, 2H), 3.05 (s, 3H). MS: m/z=489.3 (M+1), HPLC: 93.67% (method B).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford crude product
  3. extractionextracted with ethyl acetate (2×25 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ff74954c89784a45a2a2b77d0aa63a71
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353107B2

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