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

HRID 1767699

반응식

HRID 1767699 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 temparature 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)+

후처리

  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

출처 및 근거

ORD 기록
ord-3c60b4716c8b419b9da454c0f879bf7a
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235558B2

연결된 노트

불러오는 중…