HCID 67345592, compound → HCID 67324676, compound

HRID 1257655Notes

Reaction equation

HRID 1257655 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:32]([O-])=O)[C:18]([NH:19][C@@H:20]4[CH2:24][CH2:23][N:22]([CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[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>C(OCC)(=O)C.[Ni]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:32])[C:18]([NH:19][C@@H:20]4[CH2:24][CH2:23][N:22]([CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 67345592HCID 67345592, compound

Product 1

HCID 67324676HCID 67324676, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-((R)-1-benzyl-pyrrolidin-3-yl)-amine (2.48 g, 5.2 mmol) and Raney Ni (5.5 g) in ethyl acetate (50 mL) was hydrogenated at 25° C. for 2.5 hours. The mixture was filtered through Celite, thoroughly washing the filter cake with methanol. The filtrate and washings were combined and concentrated under vacuum, gave 2.2 g (96%) of (1-Benzenesulfonyl-5-amino-1H-pyrrolo[2,3-b]pyridin-4-yl)-((R)-1-benzyl-pyrrolidin-3-yl)-amine, which was used in the next step without further purification. LCMS (Method J, ESI): RT=0.81 min, M+H+=447.9; 1H NMR (400 MHz, CDCl3) δ: 8.07-8.05 (d, J=6.8 Hz, 2H), 7.74 (s, 1H), 7.46-7.44 (m, 2H), 7.39-7.35 (m, 3H), 7.25-7.18 (m, 6H), 6.52-6.50 (d, J=4.4 Hz, 1H), 4.30-4.40 (m, 1H), 3.56 (s, 2H), 2.79-2.76 (m, 2H), 2.69-2.59 (m, 1H), 2.36-2.25 (m, 2H), 1.60-1.70 (m, 1H).

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-3e0aa0db76dd49a5aaea5d4cc74b84f5
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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