HCID 60166868, compound → HCID 67343618, compound

HRID 1257576Notes

Reaction equation

HRID 1257576 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[C:18]([N+:19]([O-])=O)=[CH:17][N:16]=[C:15]3[N:22]([S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])=[O:26])[CH:23]=[CH:24][C:14]=23)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:12][C:13]2[C:18]([NH2:19])=[CH:17][N:16]=[C:15]3[N:22]([S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])=[O:26])[CH:23]=[CH:24][C:14]=23)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 60166868HCID 60166868, compound

Product 1

HCID 67343618HCID 67343618, compoundYield 125%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (425 mg, 898 μmol) in THF (15 ml) containing palladium (10% on carbon, 95.0 mg, 90.0 μmol) was stirred at ambient temperature under a hydrogen atmosphere for 24 hours. The mixture was filtered through Celite®, the filter cake thoroughly washed with THF, and the combined filtrates concentrated under vacuum to give 498 mg of 3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-azetidine-1-carboxylic acid tert-butyl ester, which was used without further purification. LCMS (Method B, ESI): RT=4.04 min, m+H=444.4.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe filter cake thoroughly washed with THF
  3. concentrationthe combined filtrates concentrated under vacuum

Sources & evidence

ORD record
ord-31eec08418564f31b17b4d2f7ec45d07
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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