HCID 178428725, compound → 1,1-Dimethylethyl 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2059938Notes

Reaction equation

HRID 2059938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][NH:15][C:16](=[NH:35])[C:17]2[C:18]([CH3:34])=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH2:23][N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:21][CH2:20]3)=O)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:14][N:15]=[C:16]([C:17]3[C:18]([CH3:34])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH2:23][N:22]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:21][CH2:20]4)[N:35]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

3

Reactant 1

HCID 178428725HCID 178428725, compound

Product 1

HCID 575058381,1-Dimethylethyl 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylateYield 55.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl 6-[{[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)oxy]amino}(imino)methyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 18; 413 mg; 0.823 mmol) in 1,4-dioxane (15 ml) was stirred at 110° C. for ca. 18 h. The mixture was cooled to room temperature and the solvent removed. Purification by flash chromatography on silica gel, eluting with 5-25% ethyl acetate in cyclohexane followed by 13-63% ethyl acetate in cyclohexane, gave the title compound as a white foam (220 mg).

Workup

  1. customthe solvent removed
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 5-25% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-2cfadb5796c44202a1963096b2853382
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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