Triethylamine → HCID 66625277, compound

HRID 2167243Notes

Reaction equation

HRID 2167243 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C@@H:7]([CH3:12])[CH2:6][C@H:5]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1.C(N(CC)CC)C.[CH:28]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[Cl-].[NH4+]>ClCCl>[CH:28]1([C:34]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([F:1])=[CH:11][CH:10]=3)[C@H:5]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:6][C@@H:7]2[CH3:12])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 75938Cyclohexanecarbonyl chlorideHCID 66625629HCID 66625629, compound

Product 1

HCID 66625277HCID 66625277, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

88 mg of cis-6-fluoro-4-[(4-fluorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 3 mL of dichloromethane, and 117 mg of triethylamine and 168 mg of cyclohexanecarbonyl chloride were added to the solution under ice cooling. The mixture was stirred for 16 hours under ice cooling. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added to the reaction liquid, and the mixture was extracted with dichloromethane. Subsequently, the extraction product was dehydrated over anhydrous magnesium sulfate, and then was concentrated under reduced pressure. The resulting residue was subjected to recrystallization using chloroform, and thus 21 mg (17%) of the title compound was obtained as a colorless flake-shaped crystal.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with dichloromethane
  3. concentrationwas concentrated under reduced pressure
  4. customThe resulting residue was subjected to recrystallization

Sources & evidence

ORD record
ord-5e0340e9052e4d919da27523c229114a
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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