Trifluoroacetic acid → 2-amino-N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)-amino]pyridin-3-yl}ethanesulfonamide

HRID 1504893Notes

Reaction equation

HRID 1504893 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][S:10]([CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)(=[O:12])=[O:11])=[CH:5][C:4]=1[NH:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[N:25]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[NH2:15][CH2:14][CH2:13][S:10]([NH:9][C:6]1[CH:7]=[N:8][C:3]([C:1]#[N:2])=[C:4]([NH:23][C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[N:25]=2)[CH:5]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734337Tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate

Product 1

HCID 867317672-amino-N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)-amino]pyridin-3-yl}ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate (100 mg, 0.22 mmol) in dichloromethane (1.8 mL) was added trifluoroacetic acid (0.26 mL, 3.4 mmol). The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure to afford 2-amino-N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}ethanesulfonamide, which was used without further purification. MS ESI calc'd. for C15H19N6O2S [M+H]+ 347. found 347.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-21499b3f51c242f88d53a1e6315cd240
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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