Carbamic acid, N-[[3-[4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]phenyl]methyl]-, 1,1-dimethylethyl ester → (3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanamine

HRID 1625485Notes

Reaction equation

HRID 1625485 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=3)[CH2:14][NH:15]C(=O)OC(C)(C)C)[C:3]=12>Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:14][NH2:15])[CH:23]=[CH:24][CH:25]=3)[C:3]=12

Participants

4

Reactant 1

HCID 59362517Carbamic acid, N-[[3-[4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]phenyl]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 59362394(3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanamineYield 77.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl 3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzylcarbamate (50 mg) was dissolved in a solution of HCl in ethyl acetate, the reaction solution was stirred at room temperature overnight, the most of solvent was removed on a rotary evaporator and filtered to give the 31 mg of (3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanamine as HCl salt. yield: 72.1%.

Workup

  1. customthe most of solvent was removed on a rotary evaporator
  2. filtrationfiltered

Sources & evidence

ORD record
ord-0dce25e49b424d8abc21a559831b017d
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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