Pyridine → HCID 56966131, compound

HRID 1036946Notes

Reaction equation

HRID 1036946 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][CH:31]([S:33](Cl)(=[O:35])=[O:34])[CH3:32]>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:33]([CH:31]([CH3:32])[CH3:30])(=[O:35])=[O:34])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 672916153-(4,4-Dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966131HCID 56966131, compoundYield 77.8%

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 (0.23 mL, 2.81 mmol) and dichloromethane (1.5 mL) at 0° C. was added dropwise a solution of propane-2-sulfonyl chloride (200 mg, 1.40 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 propane-2-sulfonic acid [3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide (155 mg, 77.8%) as a white solid. MS (ESI+APCI) M+1=427.2.

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-b53455888dc54824a020b69dbbdd3531
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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