Triethylamine → 4-Amino-N-(4-aminophenyl)-2-methyl-6-quinolinecarboxamide

HRID 19514

Reaction equation

HRID 19514 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=O)[CH:10]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.C(OC([NH:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)=O)(C)(C)C.C(N(CC)CC)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([NH:23][C:24]3[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=3)=[O:14])[CH:10]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 71379804-Amino-2-methylquinoline-6-carboxylic acid

Product 1

HCID 178646204-Amino-N-(4-aminophenyl)-2-methyl-6-quinolinecarboxamideYield 29.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 270 mg (1.0 mmol) 4-amino-2-methyl-6-quinolincarboxylic acid, 220 mg (1.1 mmol) 4-t-butoxycarbonylaminoaniline, and 0.56 ml (4.0 mmol) triethylamine in 10 ml DMF was added 4.42 mg (1.0 mmol) BOP reagent. After 1 h stirring at room temperature the solution was evaporated. The residue was dissolved in 1M solution of NaOH and extracted with ethyl acetate and the organic layer was washed with water and brine, dried (MgSO4) and evaporated. The residue was treated with 4M HCl in dioxane at room temperature for 1 h. After evaporation the residue was purified by HPLC and lyophilized to give 86 mg (17%) of the title compound. MS 293.3 (M+H)+

Workup

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in 1M solution of NaOH
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. additionThe residue was treated with 4M HCl in dioxane at room temperature for 1 h
  8. customAfter evaporation the residue
  9. customwas purified by HPLC

Sources & evidence

ORD record
ord-222f3fecb60948be81763edec7341b4d
Source dataset
uspto-grants-2010_06
Patent number
US07745443B2

Linked notes

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