Hydrochloric Acid → HCID 58916337, compound

HRID 2221153Notes

Reaction equation

HRID 2221153 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:25]=[C:24]4[C:19]([N:20]=[CH:21][C:22]([O:26]CCO)=[N:23]4)=[CH:18][CH:17]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1.C(N[CH:34]([CH3:36])C)(C)C.CS([Cl:41])(=O)=O.Cl>ClCCl.C(Cl)(Cl)Cl.C(O)(C)C.N1C=CC=CC=1>[Cl:41][CH2:34][CH2:36][N:23]1[C:24]2[C:19](=[CH:18][CH:17]=[C:16]([C:9]3[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=4)=[N:12][N:11]4[CH2:13][CH2:14][CH2:15][C:10]=34)[CH:25]=2)[N:20]=[CH:21][C:22]1=[O:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 31297Methanesulfonyl chlorideHCID 10023092HCID 10023092, compound

Product 1

HCID 58916337HCID 58916337, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Cool a solution of 2-{7-[2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoxalin-2-yloxy}-ethanol (0.5 g, 1.3 mmol) and diisopropylamine (0.5 ml) in dry dichloromethane (10 mL) to −30° C. Add methanesulfonylchloride (0.5 ml) dropwise to the solution and stir the resulting mixture for 30 min while allowing the reaction mixture to warm to room temperature. Add 5 N hydrochloric acid (0.2 mL) and pyridine (1 mL) to the mixture and heat at 80° C. for 3 h. Dilute the reaction mixture with 1:1 chloroform/isopropyl alcohol and wash the solution with saturated sodium chloride solution. Dry the organic layer (sodium sulfate), filter, and evaporate the solvents. Purify the residue by silica gel chromatography (dichloromethane to 1:1 dichloromethane/methanol) to give 274 mg (68%) of the titled compound. MS ES+ 407 (M+1).

Workup

  1. temperatureheat at 80° C. for 3 h
  2. washwash the solution with saturated sodium chloride solution
  3. dry with materialDry the organic layer (sodium sulfate)
  4. filtrationfilter
  5. customevaporate the solvents
  6. customPurify the residue by silica gel chromatography (dichloromethane to 1:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-15073be77e1c4664b382a87a733962ca
Source dataset
uspto-grants-2008_05
Patent number
US07368445B2

Reaction notes

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