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

HRID 19514

反応式

HRID 19514 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-222f3fecb60948be81763edec7341b4d
出典データセット
uspto-grants-2010_06
特許番号
US07745443B2

関連ノート

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