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Pyridine → cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-dimethoxy-3,4 dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester

HRID 1530893
Notes
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Reaction equation

HRID 1530893 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)[C:13]2[C:8](=[CH:9][C:10]([O:34][CH3:35])=[C:11]([O:32][CH3:33])[CH:12]=2)[N:7]1[C:36]([O:38][CH:39]([CH2:41][CH3:42])[CH3:40])=[O:37])=[O:5])[CH3:2].N1C=CC=CC=1.Cl[C:50]([O:52][CH3:53])=[O:51]>ClCCl.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([N:16]([CH2:17][C:18]2[CH:19]=[C:20]([C:28]([F:31])([F:29])[F:30])[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=2)[C:50]([O:52][CH3:53])=[O:51])[C:13]2[C:8](=[CH:9][C:10]([O:34][CH3:35])=[C:11]([O:32][CH3:33])[CH:12]=2)[N:7]1[C:36]([O:38][CH:39]([CH2:41][CH3:42])[CH3:40])=[O:37])=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 86592229HCID 86592229, compound

Product 1

HCID 86592230cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-dimethoxy-3,4 dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl esterYield 72.5%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-6,7-dimethoxy-3,4-dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester (Example 4) (approximately 500 mg, 0.83 mmol) and pyridine (195 mg, 2.5 mmol) were dissolved in anhydrous dichloromethane (100 mL) and cooled to 0° C. Methyl chloroformate (195 mg, 2.1 mmol) was added slowly. The reaction was stirred at 0° C. for 1 h, then at room temperature for 18 h. The reaction mixture was then diluted with chloroform, and washed with 1N HCl. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 15% ethyl acetate/hexanes as eluent afforded the title product (400 mg). MS m/z 664.2 (M+); 1H NMR (CDCl3) δ 0.9 (t, 3H), 1.3 (t, 3H), 1.5 (m, 2H), 3.85 (s, 3H), 4.0 (t, 2H) 6.3 (s, 1 H), 7.8 (s, 1H).

Workup

  1. waitat room temperature for 18 h
  2. washwashed with 1N HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-821cfa80c9fe468b99d42025d0f370df
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197786B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes