Dimethylformamide → HCID 59591088, compound

HRID 2383317Notes

Reaction equation

HRID 2383317 reaction equation
O[NH:2][C:3](=[NH:30])[C:4]1[C:5]([CH3:29])=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([CH2:14][CH2:15][CH2:16][C:17](=[O:21])CCC)[N:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8][CH2:7]2.C(N([CH2:36][CH3:37])CC)C.[Cl:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[O:48][CH:49]([CH3:51])[CH3:50])[C:42](Cl)=[O:43].CN(C)C=[O:55]>>[Cl:38][C:39]1[CH:40]=[C:41]([C:42]2[O:43][N:2]=[C:3]([C:4]3[C:5]([CH3:29])=[C:6]4[C:11](=[CH:12][CH:13]=3)[CH:10]([CH2:14][CH2:15][CH2:16][C:17]([O:21][CH2:36][CH3:37])=[O:55])[N:9]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:8][CH2:7]4)[N:30]=2)[CH:45]=[CH:46][C:47]=1[O:48][CH:49]([CH3:51])[CH3:50]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 21710470HCID 21710470, compoundHCID 178450444HCID 178450444, compound

Product 1

HCID 59591088HCID 59591088, compound

Procedure

To a solution of 1,1-dimethylethyl 6-[(hydroxyamino)(imino)methyl]-5-methyl-1-(4-oxoheptyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 27; 230 mg, 0.551 mmol) in N,N-Dimethylformamide (DMF) (5 ml) was added triethylamine (0.115 ml, 0.826 mmol) followed by 3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride (Preparation 33; 154 mg, 0.661 mmol) in DMF (2 ml) dropwise over one minute at room temperature under nitrogen. The resulting mixture was stirred for 1 h at room temperature, then heated at 120° C. for ca. 2.5 h. Most of the solvent was removed and the residue dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate then brine, dried over MgSO4 and concentrated in vacuo to give the crude product (ca. 350 mg). Purification by flash chromatography on silica gel, eluting with 5-25% ethyl acetate in cyclohexane gave the title compound (110 mg) as a colourless oil.

Workup

  1. temperatureheated at 120° C. for ca. 2.5 h
  2. customMost of the solvent was removed
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe solution was washed with saturated aqueous sodium bicarbonate
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give the crude product (ca. 350 mg)
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 5-25% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-7bf48b1b8f444501a055f71fa942fcae
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

Loading…