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

HRID 531481Notes

Reaction equation

HRID 531481 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ff74954c89784a45a2a2b77d0aa63a71
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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