Pyridine → HCID 56966128, compound

HRID 1036943Notes

Reaction equation

HRID 1036943 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:17]=[C:18]([NH:22][S:31]([CH3:30])(=[O:33])=[O:32])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 672916153-(4,4-Dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966128HCID 56966128, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (150 mg, 0.49 mmol) in pyridine (74 mg, 0.94 mmol) and dichloromethane (1.5 mL) at 0° C. was added dropwise a solution of methanesulfonyl chloride (80 mg, 0.70 mmol) in dichloromethane (0.5 mL). The mixture was stirred at room temperature overnight. The mixture was quenched with water (5 mL) and extracted with dichloromethane (5 mL×2). The combined organic layers were dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel to afford N-[3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-methanesulfonamide (120 mg, 64.5%) as a white solid. MS (ESI+APCI) M+1=399.1.

Workup

  1. customThe mixture was quenched with water (5 mL)
  2. extractionextracted with dichloromethane (5 mL×2)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-565220f0cbe7406787e0b14892bc7924
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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