HCID 67342783, compound → HCID 67343959, compound

HRID 1257750Notes

Reaction equation

HRID 1257750 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([NH:18][C:19]2[C:24]([N+:25]([O-])=O)=[CH:23][N:22]=[C:21]3[N:28]([S:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)(=[O:33])=[O:32])[CH:29]=[CH:30][C:20]=23)([CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Ni]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([NH:18][C:19]2[C:24]([NH2:25])=[CH:23][N:22]=[C:21]3[N:28]([S:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)(=[O:33])=[O:32])[CH:29]=[CH:30][C:20]=23)([CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67342783HCID 67342783, compound

Product 1

HCID 67343959HCID 67343959, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(1-Benzene sulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-methyl-piperidine-1-carboxylic acid benzyl ester (400 mg, 0.73 mmol) and Raney Ni (1.0 g) in ethyl acetate (20 mL) was hydrogenated at 25° C. for 1.5 hours. The mixture was filtered through Celite, thoroughly washing the filter cake with methanol. The filtrate and washings were combined and concentrated under vacuum to give about 380 mg (100%) of 3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-methyl-piperidine-1-carboxyli c acid benzyl ester without further purification. LCMS (Method J, ESI): RT=1.04 min, m+H=519.8.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthoroughly washing the filter cake with methanol
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c2293c3ea7eb46db831007e6516e3cd4
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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