Ethylmorpholine → 3-Amino-N-(4-amino-2-methyl-quinolin-6-yl)-propionamide

HRID 1767696

反応式

HRID 1767696 の反応式
C(OC(NCCC(O)=O)=O)(C)(C)C.[B-](F)(F)(F)F.CCO[C:22]([C:24]([C:34]#[N:35])=NOC(N(C)C)=[N+](C)C)=[O:23].[CH3:36][C:37]1[CH:46]=[C:45]([NH2:47])[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([NH2:48])[CH:43]=2)[N:38]=1.C(N1CCOCC1)C>CN(C=O)C>[NH2:35][CH2:34][CH2:24][C:22]([NH:48][C:42]1[CH:43]=[C:44]2[C:39](=[CH:40][CH:41]=1)[N:38]=[C:37]([CH3:36])[CH:46]=[C:45]2[NH2:47])=[O:23]

参加物

6

反応物 4

HCID 7525EthylmorpholineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 2239952-Methylquinoline-4,6-diamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 178646293-Amino-N-(4-amino-2-methyl-quinolin-6-yl)-propionamide収率 182.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2.18 g (11.55 mmol) of 3-tert-Butoxycarbonylamino-propionic acid in 20 ml of DMF were added 3.78 g (11.55 mmol) TOTU. After 15 min at room temperature 2.0 g (11.55 mmol) of 2-methyl-quinoline-4,6-diamine and 2.66 g (23 mmol) of N-ethylmorpholine were added. After 24 h stirring at room temperature the solution was evaporated and the residue was treated with a saturated aqueous solution of NaHCO3. The aqueous solution was extracted with ethyl acetate. The separated organic layer was dried (Na2SO4) and evaporated. The residue was treated with 20 ml 90% trifluoroacetic acid for 2 h. After evaporation the residue was dissolve in water and extracted with ethyl acetate. The aqueous layer was lyophilized to yield 5.15 g (76%) of the title compound. MS 245.1 (M+)+.

後処理

  1. customwas evaporated
  2. additionthe residue was treated with a saturated aqueous solution of NaHCO3
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. dry with materialThe separated organic layer was dried (Na2SO4)
  5. customevaporated
  6. additionThe residue was treated with 20 ml 90% trifluoroacetic acid for 2 h
  7. customAfter evaporation the residue
  8. dissolutionwas dissolve in water
  9. extractionextracted with ethyl acetate

出典と根拠

ORDレコード
ord-a5449293a62540a09e31aa2ff2515340
出典データセット
uspto-grants-2007_06
特許番号
US07235558B2

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