Hydrochloric Acid → HCID 69312784, compound

HRID 2219015Notes

Reaction equation

HRID 2219015 reaction equation
[C:1]1([S:11]([C:14]2[C:24]3[C:25]4[N:16]([CH2:17][CH2:18][O:19][C:20]=4[CH:21]=[C:22]([O:26][CH2:27][CH2:28]O)[CH:23]=3)[N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CS(OS(C)(=O)=O)(=O)=O.[CH2:39]([N:41](CC)CC)C.CN.[ClH:48].CCOCC>C(Cl)Cl.CS(C)=O.O>[ClH:48].[CH3:39][NH:41][CH2:28][CH2:27][O:26][C:22]1[CH:23]=[C:24]2[C:25]3=[C:20]([O:19][CH2:18][CH2:17][N:16]3[N:15]=[C:14]2[S:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:13])=[O:12])[CH:21]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6329MethylamineHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 59771311HCID 59771311, compound

Product 1

HCID 69312784HCID 69312784, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(naphthalene-1-sulfonyl)-7,8-dihydro-6-oxa-1,8a-diaza-acenaphthylen-4-yloxy]ethanol (0.41 g, 1.0 mmoles), methane sulfonic anhydride (Ms2O) (0.176 g, 1.05 mmoles) and triethylamine (0.143 ml, 1.05 mmole) in CH2Cl2 was stirred at 0° C. to room temperature for 5 hours and concentrated in vacuo to give a residue. A mixture of the residue and methylamine (0.5 ml of 1M solution in THF, 0.5 mmoles) in DMSO was stirred overnight at 70° C., cooled to room temperature, diluted with water and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by flash chromatography using as eluent 5% CH3OH/EtOAc. The purified compound was dissolved in methanol, treated with 1M HCl in ether (0.2 ml, 0.2 mmoles) and evaporated to dryness to afford the title product as a dark pale solid, identified by HNMR and mass spectral analyses, MS: (ES) m/z 423.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a residue
  3. stirringwas stirred overnight at 70° C.
  4. extractionextracted with EtOAc
  5. washwashed sequentially with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe resultant residue was purified by flash chromatography
  9. dissolutionThe purified compound was dissolved in methanol
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-0407957408b3437b84c80ddc059cbf1b
Source dataset
uspto-grants-2008_08
Patent number
US07414051B2

Reaction notes

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