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

HRID 1257744Notes

Reaction equation

HRID 1257744 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:27]([O-])=O)[C:18]([NH:19][C@@H:20]4[CH2:25][CH2:24][CH2:23][C@@H:22]([OH:26])[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.[H][H]>C(O)(C)C.[Pd]>[NH2:27][C:17]1[C:18]([NH:19][C@@H:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([OH:26])[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

5

Reactant 2

HCID 67352793(1R,3R)-3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino) cyclohexanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67351524(1R,3R)-3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To the reaction mixture from the above step containing (1R,3R)-3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino) cyclohexanol (8.65 mmol) in isopropyl alcohol (30 mL) was added 10% Palladium on activated carbon (718 mg). The reaction mixture was then capped with a 3 way glass valve with a hydrogen gas balloon. The flask was opened to vacuum for two minutes, followed by opening to hydrogen. This purge/flush cycle was repeated 3 times before stirring under a hydrogen atmosphere at room temperature for 2 days. LC/MS showed that the reaction went to completion. The reaction mixture was then filtered through celite 545 and concentrated to give a black foamy solid, which was used as is for the next step. LCMS (Method M, ESI): RT=1.44 min, m+H=386.8.

Workup

  1. filtrationThe reaction mixture was then filtered through celite 545
  2. concentrationconcentrated
  3. customto give a black foamy solid, which

Sources & evidence

ORD record
ord-e4bf116c43bd4c5aaa1560c9133520f3
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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