Water → HCID 66625213, compound

HRID 2167238Notes

Reaction equation

HRID 2167238 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C@@H:9]([CH3:12])[CH2:8][C@H:7]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20].[C:21](Cl)(=[O:23])[CH3:22].O>N1C=CC=CC=1.ClCCl>[C:21]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[F:1])[C@H:7]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH2:8][C@@H:9]1[CH3:12])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 66625286HCID 66625286, compound

Product 1

HCID 66625213HCID 66625213, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

[Step 2] 60 mg of cis-8-fluoro-4-[(2-fluorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 0.5 mL of pyridine and 2 mL of dichloromethane, and 16 mg of acetyl chloride was added to the solution under ice cooling. The resulting mixture was stirred for 2 hour under ice cooling. After completion of the reaction, water was added to the reaction liquid, the mixture was extracted with chloroform, and then the organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine. The washed organic layer was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (chloroform), and thus 48 mg (70%) of the title compound was obtained as a colorless oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionthe mixture was extracted with chloroform
  3. washthe organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine
  4. concentrationwas concentrated under reduced pressure
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-ee19b49291674b2f93d33895590b4203
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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