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

HRID 531482Notes

Reaction equation

HRID 531482 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH:10]=[N:9]1)([O-])=O.[H][H]>[Pd].C1COCC1.CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH:10]=[N:9]1

Participants

5

Reactant 2

HCID 72944751N-(3-(3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 72944850N-(3-(3-(1-(3-aminobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamideYield 16.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

N-(3-(3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (Example-7) (80 mg, 0.163 mmol), was reduced by palladium on carbon (8 mg, 10% W/W) in THF/MeOH (2/2 mL) under positive pressure of hydrogen using a bladder. The catalyst filtered off and concentrated to get crude compound. This was then purified by preparative TLC using 10% ethyl acetate in hexanes as eluent yielded 12 mg (16% yield) of pure titled compound. 1H NMR (DMSO-d6, 400 MHz): δ11.85 (s, 1H), 9.83 (s, 1H), 8.47-8.46 (d, 1H), 8.33-8.32 (m, 2H), 7.92 (s, 1H), 7.775-7.770 (d, 1H), 7.53-7.44 (m, 3H), 7.24-7.22 (d, 1H), 6.96-6.94 (t, 1H), 6.46-6.42 (m, 2H), 5.20 (s, 2H), 5.10 (b, 2H), 3.05 (s, 3H). MS: m/z=459.3 (M+1), HPLC: 92.06% (method B).

Workup

  1. filtrationThe catalyst filtered off
  2. concentrationconcentrated
  3. customto get crude compound
  4. customThis was then purified by preparative TLC

Sources & evidence

ORD record
ord-61dd0093d3d44770918e7e5a43de3db8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…