Aniline → HCID 750059, compound

HRID 488927Notes

Reaction equation

HRID 488927 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2OS(C(F)(F)F)(=O)=O)[S:4][C:3]=1[C:19](=[O:21])[NH2:20].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.CO.C(Cl)Cl>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:4][C:3]=1[C:19]([NH2:20])=[O:21]

Participants

5

Reactant 2

HCID 6115AnilineHCID 23401030HCID 23401030, compound

Product 1

HCID 750059HCID 750059, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent2×

Procedure

A solution of 20 mg trifluoromethanesulfonic acid 3-amino-2-carbamoyl-thieno[2,3-b]pyridin-4-yl ester and 27 microL aniline in 1 mL of THF was heated at 55° C. overnight under Ar. The reaction was applied to a 2 mm silica gel prep plate that was developed twice in 5% MeOH—CH2Cl2. The band was eluted with 50% MeOH—CH2Cl2 to get 18 mg. This was dissolved in 5% MeOH—CH2Cl2, filtered, concentrated, and dried in vacuo at 60° C. overnight to provide 10.5 mg of the title compound as a yellow-green solid.

Workup

  1. washThe band was eluted with 50% MeOH—CH2Cl2
  2. customto get 18 mg
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-f0ada64cb74542f8b36730f3eec744ce
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

Loading…