Pyridine → HCID 69694785, compound

HRID 1071706Notes

Reaction equation

HRID 1071706 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]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][C@@H:7]1[CH:28]([CH3:30])[CH3:29])=[O:5])[CH3:2].N1C=CC=CC=1.Cl[C:38]([O:40][CH3:41])=[O:39].[OH-].[K+]>ClCCl.O>[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]([N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:38]([O:40][CH3:41])=[O:39])[CH2:8][C@@H:7]1[CH:28]([CH3:29])[CH3:30])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 14797Potassium HydroxideHCID 69694549HCID 69694549, compound

Product 1

HCID 69694785HCID 69694785, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-4-benzylamino-6,7-dimethoxy-2-isopropyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 93) (22 mg, 0.05 mmol) and pyridine (0.50 mL, 6.2 mmol) in anhydrous dichloromethane (1 mL) was added methyl chloroformate (0.10 mL, 1.3 mmol) while cooled in an ice bath. After stirring at room temperature overnight, water (10 mL), and aqueous 2N KOH (10 mL) were added to the reaction mixture. The solution was stirred for 30 min, then the mixture was extracted with ethyl acetate (2×10 mL). The organic phases were combined and washed with 1N HCl (2×10 mL), a saturated sodium bicarbonate solution (10 mL), and brine (10 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 88 mg crude product. Purification by silica gel chromatography using 0-40% ethyl acetate/hexanes as eluent afforded the title product (12 mg, 50%). MS m/z 471 (M++1), 488 (M++18); 1H NMR (CDCl3) δ 0.6-0.8 (m, 6H), 1.25 (t, 3H), 1.4 (m, 1H), 1.8-2.3 (m, 3H), 3.8 (s, 6H), 3.85 (s, 3H), 4.0-4.3 (m, 5H), 5.1 (m, 1H), 6.96 (C8, bs, 1H), 6.42 (C5, bs, 1H), 7.2-7.4 (m, 5H).

Workup

  1. temperaturewhile cooled in an ice bath
  2. stirringThe solution was stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate (2×10 mL)
  4. washwashed with 1N HCl (2×10 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give 88 mg crude product
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c8b0f68639d1481988fa6433939af135
Source dataset
uspto-grants-2005_06
Patent number
US06906082B2

Reaction notes

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