Ammonia → HCID 86755980, compound

HRID 369918Notes

Reaction equation

HRID 369918 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=2)[C@H:9]([N:20]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[C:21](Cl)=[O:22])[CH2:8][C@@H:7]1[CH3:39])=[O:5])[CH3:2].[NH3:40]>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=2)[C@H:9]([N:20]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[C:21]([NH2:40])=[O:22])[CH2:8][C@@H:7]1[CH3:39])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86755978HCID 86755978, compound

Product 1

HCID 86755980HCID 86755980, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-chlorocarbonyl-amino]-2-methyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester. (Example 50A) (125 mg) was dissolved in dichloromethane (4 mL), and cooled in an ice water bath as gasous ammonia was condensed into the solution. After stirring overnight at room temperature, the reaction mixture was quenched with 10 mL of 1N HCl and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with 10 mL saturated sodium bicarbonate, 10 mL of brine, dried over sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 0-50% ethyl acetate/hexanes as eluent afforded the title product (0.091 g, 76%). MS m/z 563 (M+ +1); 1H NMR (CDCl3) δ 1.18 (Me, d, 3H, J=5.9 Hz), 1.2-1.4 (m, 4H), 2.1-2.2 (m, 1H), 4.1-4.3 (m, 3H), 4.3-4.5 (m, 1H), 4.9 (bs, 2H), 5.0-5.3 (m, 3H), 7.20 (C5, s, 1H), 7.5 (d, 1H), 7.6 (d, 1H), 7.75 (s, 2H), 7.8 (s, 1H).

Workup

  1. customcondensed into the solution
  2. customthe reaction mixture was quenched with 10 mL of 1N HCl
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washThe combined organic layers were washed with 10 mL saturated sodium bicarbonate, 10 mL of brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-2f2a61fecd014e44a83e941241adc40c
Source dataset
uspto-grants-2000_10
Patent number
US06140343

Reaction notes

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