Pyridine → HCID 86756028, compound

HRID 1937464Notes

Reaction equation

HRID 1937464 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([NH:21][CH2:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=3)[CH2:10][C@H:11]([CH3:20])[N:12]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=1[O:37][CH3:38])=[O:4].N1C=CC=CC=1.Cl[C:46]([O:48][CH3:49])=[O:47]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([N:21]([CH2:22][C:23]3[CH:24]=[C:25]([C:33]([F:34])([F:36])[F:35])[CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=3)[C:46]([O:48][CH3:49])=[O:47])[CH2:10][C@H:11]([CH3:20])[N:12]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=1[O:37][CH3:38])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 86756020HCID 86756020, compound

Product 1

HCID 86756028HCID 86756028, compoundYield 135.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1,7-dicarboxylic acid 1-ethyl ester 7-methyl ester (335 mg, 0.61 mmol) was dissolved in anhydrous dichloromethane (5 mL), and pyridine (0.20 mL, 2.5 mmol) was added. Methyl chloroformate (0.057 mL, 0.73 mmol) was slowly added and the reaction was stirred at room temperature for 3 h. Additional aliquots of reagents were added to drive the reaction to completion. The reaction mixture was then diluted with 35 ml dichloromethane, washed with an aqueous 1N HCl solution (2×7 mL) and with a saturated sodium bicarbonate solution (2×7 mL) saturated NaHCO3. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 20% acetone/hexanes as eluent afforded the title product (0.50 g, 90%). MS m/z 607 (M++1); 1H NMR (CDCl3) δ 1.5-1.75 (br, 1H), 6.42 (s, 1H).

Workup

  1. additionAdditional aliquots of reagents were added
  2. customthe reaction to completion
  3. washwashed with an aqueous 1N HCl solution (2×7 mL) and with a saturated sodium bicarbonate solution (2×7 mL) saturated NaHCO3
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-fbbff8b458a04fde82bb84ec94e97922
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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