4-Nitroaniline → HCID 10019440, compound

HRID 488928Notes

Reaction equation

HRID 488928 reaction equation
COC(=O)CO[C:6]1[N:11]=[C:10]2[S:12][C:13]([C:16](=[O:18])[NH2:17])=[C:14]([NH2:15])[C:9]2=[C:8](C)[CH:7]=1.[N+:21]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)([O-:23])=[O:22]>O1CCOCC1>[NH2:15][C:14]1[C:9]2[C:10](=[N:11][CH:6]=[CH:7][C:8]=2[NH:28][C:27]2[CH:29]=[CH:30][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)[S:12][C:13]=1[C:16]([NH2:17])=[O:18]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 9994643HCID 9994643, compound

Product 1

HCID 10019440HCID 10019440, compoundYield 9.9%

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-62db7ed8f332492185d7d8afc9207fdb
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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