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

HRID 19511

Reaction equation

HRID 19511 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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+1)+.

Workup

  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

Sources & evidence

ORD record
ord-99c24b8d550d47829af6789f822fc3fc
Source dataset
uspto-grants-2010_06
Patent number
US07745443B2

Linked notes

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