1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → cis-4-[2-(3,5-Bis-trifluoromethyl-phenyl)-acetylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 369919

Reaction equation

HRID 369919 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([NH2:20])[CH2:8][C@@H:7]1[CH3:21])=[O:5])[CH3:2].[F:22][C:23]([F:39])([F:38])[C:24]1[CH:25]=[C:26]([CH2:34][C:35](O)=[O:36])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1.CN(C)CCCN=C=NCC>ClCCl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([NH:20][C:35](=[O:36])[CH2:34][C:26]2[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=[C:24]([C:23]([F:38])([F:22])[F:39])[CH:25]=2)[CH2:8][C@@H:7]1[CH3:21])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acidHCID 69832909cis-4-amino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

Product 1

HCID 86755981cis-4-[2-(3,5-Bis-trifluoromethyl-phenyl)-acetylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cis-4-amino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (150 mg, 0.50 mmol) and 3,5-bis-trifluoromethylphenylacetic acid (138 mg, 0.51 mmol) in 1.5 ml anhydrous dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (192 mg, 0.66 mmol) and the resulting solution was stirred at room temperature overnight. The reaction mixture was diluted with 50 ml ethyl acetate and was washed with 0.1N HCl (2×10 mL), 0.1N NaOH (2×10 mL) and brine (1×10 mL). The organic phase was dried (MgSO4), filtered and concentrated, and the the residue was chromatographed using 20:1 hexanes:ethyl acetate. The title compound crystallized out of the combined fractions (129 mg, 46%). Me 157-9° C.; MS m/z 549 (M+ +1); 1H NMR (CDCl3) δ 1.07 (d, 3H), 7.70-7.78 (m, 3H).

Workup

  1. washwas washed with 0.1N HCl (2×10 mL), 0.1N NaOH (2×10 mL) and brine (1×10 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe the residue was chromatographed
  6. customThe title compound crystallized out of the combined fractions (129 mg, 46%)
  7. customMe 157-9° C.

Sources & evidence

ORD record
ord-915341aae4ca4c189a06f1b836f8c89f
Source dataset
uspto-grants-2000_10
Patent number
US06140343

Linked notes

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