4-Nitroaniline → HCID 10019440, compound

HRID 750749Notes

Reaction equation

HRID 750749 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].[N+:22]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([O-:24])=[O:23]>O1CCOCC1>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[NH:29][C:28]2[CH:30]=[CH:31][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)[S:4][C:3]=1[C:19]([NH2:20])=[O:21]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 23401030HCID 23401030, compound

Product 1

HCID 10019440HCID 10019440, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 20 mg trifluoromethanesulfonic acid 3-amino-2-carbamoyl-thieno[2,3-b]pyridin-4-yl ester (see Example 19) and 40.5 mg 4-nitroaniline in 1 mL of dry dioxane was heated at 95° C. overnight under N2. The reaction was concentrated and applied to a 2 mm silica gel prep plate that was developed twice in 7.5% MeOH—CH2Cl2. The band was eluted with 20% MeOH—CH2Cl2, concentrated in vacuo, re-dissolved in 5% MeOH—CH2Cl2, filtered, concentrated, and dried in vacuo at 60° overnight to get 2.2 mg of the title compound as an orange solid.

Workup

  1. concentrationThe reaction was concentrated
  2. washThe band was eluted with 20% MeOH—CH2Cl2
  3. concentrationconcentrated in vacuo
  4. dissolutionre-dissolved in 5% MeOH—CH2Cl2
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuo at 60° overnight

Sources & evidence

ORD record
ord-e596e610d7e74dde803286754523ca2a
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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