Pyridine → HCID 56966061, compound

HRID 1036940Notes

Reaction equation

HRID 1036940 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.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>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:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 672916153-(4,4-Dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966061HCID 56966061, compoundYield 74.1%

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, 0.47 mmol) in pyridine (74 mg, 0.94 mmol) and dichloromethane (2 mL) at 0° C. was added dropwise a solution of ethanesulfonyl chloride (90 mg, 0.70 mol) in dichloromethane (1 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 ethanesulfonic acid [3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide (143 mg, 74.1%) as a white solid. MS (ESI+APCI) M+1=413.1.

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-e4a76a52b055456f93aa0c8264551655
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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