Trifluoroacetic acid → HCID 70664948, compound

HRID 1403331Notes

Reaction equation

HRID 1403331 reaction equation
C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:24]([N:25]([CH:27]([CH3:29])[CH3:28])[CH3:26])=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:30]([OH:32])=[O:31])[CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:24]([N:25]([CH:27]([CH3:29])[CH3:28])[CH3:26])=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:30]([OH:32])=[O:31])[CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60198400HCID 60198400, compound

Product 1

HCID 70664948HCID 70664948, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-(tert-butoxycarbonylamino)pyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid (140.0 mg, 0.32 mmol) in dichloromethane (50 mL) was added CF3COOH (182.6 mg, 1.60 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (10 mL) and adjusted to pH 6 with sodium bicarbonate. The product were collected by filtration to afford 2-(6-aminopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (88.6 mg, 78%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (10 mL)
  3. filtrationThe product were collected by filtration

Sources & evidence

ORD record
ord-618d7b38d33a48db98c091219947f514
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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