3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol → 3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol

HRID 1257755Notes

Reaction equation

HRID 1257755 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:26]([O-])=O)[C:18]([NH:19][CH:20]4[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[NH2:26][C:17]1[C:18]([NH:19][CH:20]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21]2)=[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=1

Participants

4

Reactant 1

HCID 673445193-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol

Product 1

HCID 673454333-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanolYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol (6 g, 15 mmol) in methanol (250 mL) was added palladium on carbon (1 g, 10%), then the reaction mixture was stirred at room temperature under hydrogen (45 psi) for 3 hours. The catalyst was filtered off, and the organic solution was concentrated under reduce pressure to give 4.6 g (83%) of 3-(5-Amino-1-benzene sulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol. 1H NMR (400 MHz, CDCl3) δ: 8.12-8.05 (s, 1H), 7.74 (s, 1H), 7.52-7.32 (m, 5H), 6.64-6.53 (m, 1H), 4.43-4.40 (s, 1H), 4.30-4.29 (m, 1H), 2.94-2.84 (m, 3H), 2.02-1.90 (m, 1H), 1.90-1.73 (m, 6H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe organic solution was concentrated

Sources & evidence

ORD record
ord-928e2942be9f473b9e2d7976da046db2
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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