Hydrochloric Acid → HCID 66918867, compound

HRID 1006550Notes

Reaction equation

HRID 1006550 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[N:15]([S:19]([CH2:22][CH:23](O)[CH2:24][CH2:25][CH2:26][CH3:27])(=[O:21])=[O:20])[CH:16]([CH3:18])[CH3:17].N12CCCCC1CNCC=C2.Cl>C(Cl)Cl.C(N(CC)CC)C.S(Cl)(C)(=O)=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[N:15]([S:19]([CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:20])=[O:21])[CH:16]([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22671994HCID 22671994, compoundHCID 226720701,5-Diazabicyclo[5.4.0]undecene

Product 1

HCID 66918867HCID 66918867, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 31297Methanesulfonyl chlorideSolvent

Procedure

To a solution of 2-(N-isopropyl-2-hydroxyhexylsulfonylamino)-5-trifluoromethylphenyl methoxymethyl ether (160 mg; prepared in Reference Example 31) in methylene chloride (2.0 ml), triethylamine (104 μl) and mesylchloride (35 μl) were added in a stream of argon at 0° C. The mixture was stirred for 10 minutes. To the mixture, 1,5-diazabicyclo[5,4,0]undecene (134 μl) was added. The mixture was stirred for 2 hours at room temperature. To the reaction mixture, diluted HCl was added. The mixture was extracted with ethyl acetate, washed, dried over and concentrated with the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=8:1) to give the title compound (140 mg) having the following physical data.

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed
  4. customdried over and
  5. concentrationconcentrated with the reduced pressure
  6. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=8:1)

Sources & evidence

ORD record
ord-9393d9b48c824cb8bfebf347ea3da549
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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