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Pyridine → 4-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-2-methyl-2,3,4,6,7,8-hexahydro-cyclopenta[g]quinoline-1-carboxylic acid ethyl ester

HRID 369911
Notes
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Reaction equation

HRID 369911 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][CH2:17][CH2:16][C:13]=3[CH:14]=2)[C@H:9]([NH:19][CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH2:8][C@@H:7]1[CH3:35])=[O:5])[CH3:2].N1C=CC=CC=1.[C:42](Cl)(=[O:44])[CH3:43]>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][CH2:17][CH2:16][C:13]=3[CH:14]=2)[CH:9]([N:19]([C:42](=[O:44])[CH3:43])[CH2:20][C:21]2[CH:22]=[C:23]([C:31]([F:34])([F:32])[F:33])[CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:26]=2)[CH2:8][CH:7]1[CH3:35])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86755976HCID 86755976, compound

Product 1

HCID 542258454-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-2-methyl-2,3,4,6,7,8-hexahydro-cyclopenta[g]quinoline-1-carboxylic acid ethyl esterYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of cis-4-(3,5-bis-trifluoromethyl-benzylamino)-2-methyl-2,3,4,6,7,8-hexahydro-cyclopenta[g]quinoline-1-carboxylic acid ethyl ester (Example 1E) (50 mg, 0.1 mmol) and pyridine (0.15 mL, 1.85 mmol) in dichloromethane (2.5 mL) was cooled in an ice water bath as acetyl chloride (0.2 mL, 2.8 mmol) was added by syringe. After stirring overnight at room temperature, the mixture was washed with 2N HCl, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 25% ethyl acetate/hexanes to afford 20 mg of the title compound. MS m/z 542.5 (M+); 1H NMR δ 1.1 (d, 3H), 2.3 (s, 3H), 6.8 (s, 1H), 7.3 (s, 1H).

Workup

  1. additionwas added by syringe
  2. washthe mixture was washed with 2N HCl
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4478d9e47bee4e08866b24591e106914
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06140343

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes