Triethylamine → Ethyl 3-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate

HRID 2189801Notes

Reaction equation

HRID 2189801 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6](Cl)=[O:7])#[N:2].O[NH:17][C:18](=[NH:37])[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[N:22][N:23]2[CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)CC)C>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[O:7][N:17]=[C:18]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH:21]=[N:22][N:23]4[CH2:28][C:29]([CH3:35])([CH3:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:37]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 575058423-Cyano-4-isopropoxybenzoyl chlorideHCID 178471466HCID 178471466, compound

Product 1

HCID 59316785Ethyl 3-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoateYield 68.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Cyano-4-[(1-methylethyl)oxy]benzoyl chloride (D106) (0.398 mmol) in acetonitrile (3.00 ml) at room temperature was treated with ethyl 3-{4-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}-2,2-dimethylpropanoate (D103) (101 mg, 0.332 mmol) followed by triethylamine (0.069 ml, 0.498 mmol). The resulting yellow solution was stirred at room temperature for 1 hr, refluxed overnight, for a further 24 hours and again overnight then cooled to room temperature and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [gradient ethyl acetate/cyclohexane] gave the title compound (107 mg, 68%) as a colourless solid. MS (ES) C26H27N5O4 requires 473, found 474 [M+H]+

Workup

  1. temperaturerefluxed overnight, for a further 24 hours and again overnight
  2. temperaturethen cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel [gradient ethyl acetate/cyclohexane]

Sources & evidence

ORD record
ord-28cf0ecb2b10418b827956a80eb2a495
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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