Triethylamine → Methanesulfonic acid 6-(2,4-difluoro-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester

HRID 1513882Notes

Reaction equation

HRID 1513882 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:24][CH:23]=1)=[O:21].[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(N(CC)CC)C.S(Cl)(Cl)(=O)=O>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:20](=[O:21])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=2)=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][S:38]([CH3:37])(=[O:40])=[O:39])[CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 24648Sulfuryl chlorideHCID 31297Methanesulfonyl chlorideHCID 67004951[2-(2,4-Difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 11273028Methanesulfonic acid 6-(2,4-difluoro-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve [2-(2,4-difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (540 mg, 1.11 mmoles), and methane sulfonyl chloride (254 mg, 2.22 mmoles) in 10 ml acetonitrile and add triethylamine (224 mg, 2.22 mmoles). Stir the mixture for 5 days at room temp. Add equivalent amounts of the sulfonyl chloride and triethylamine and stir for 30 minutes. Evaporate the mixture to dryness, dissolve in methanol and pass through an SCX column. Wash the column with methanol and elute the product with 2 N ammonia/methanol to yield 433 mg (69%) of the title compound: mass spectrum (ion spray) m/z=566 (M+H).

Workup

  1. stirringstir for 30 minutes
  2. customEvaporate the mixture to dryness
  3. dissolutiondissolve in methanol
  4. washWash the column with methanol
  5. washelute the product with 2 N ammonia/methanol

Sources & evidence

ORD record
ord-6c1da7add63642378dbe9e605ac9dc9b
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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