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

HRID 531481ノート

反応式

HRID 531481 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ff74954c89784a45a2a2b77d0aa63a71
出典データセット
uspto-grants-2016_05
特許番号
US09353107B2

反応ノート

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