3-Aminoquinoline → HCID 67520955, compound

HRID 1923968Notes

Reaction equation

HRID 1923968 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C(OCC)(=O)C>[N:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[C:26]([NH:25][C:10]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=2)=[O:11])[CH:27]=1

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 67520362HCID 67520362, compound

Product 1

HCID 67520955HCID 67520955, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-(trifluoromethyl)phenyl]butanoic acid V (0.97 g, 2.79 mmol) and 3-aminoquinoline VI (0.45 g, 3.10 mmol) in ethyl acetate (30 mL) was added DMT-MM (1.0 g, 3.63 mmol). After being stirred at r.t. overnight, the reaction was washed with water, 1N HCl, aq. sat. NaHCO3, water and dried over Na2SO4. The solvent was removed under reduced pressure to afford tert-butyl N-[(1R)-1-[(quinolin-3-yl)carbamoyl]-3-[4-(trifluoromethyl)phenyl]propyl]carbamate (1.23 g, 2.59 mmol, 93% yield). ESIMS found for C25H26F3N3O3 m/z 474 (M+H).

Workup

  1. washthe reaction was washed with water, 1N HCl, aq. sat. NaHCO3, water
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de1c8d79b65a4b5cb04fca43a811d3ad
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

Loading…