Acetyl chloride → HCID 86707771, compound

HRID 2410118Notes

Reaction equation

HRID 2410118 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:37][CH3:38])=[C:7]([C:9]2[N:13]([CH:14]([CH3:16])[CH3:15])[C:12]3[CH:17]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=4[CH3:36])[N:18]([C:21]4[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=4[CH3:28])[C:19](=[O:20])[C:11]=3[N:10]=2)[CH:8]=1.[C:39](Cl)(=[O:41])[CH3:40]>C1COCC1>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([CH3:28])=[C:21]([N:18]2[C:19](=[O:20])[C:11]3[N:10]=[C:9]([C:7]4[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=4[O:37][CH3:38])[CH2:2][NH:1][C:39](=[O:41])[CH3:40])[N:13]([CH:14]([CH3:15])[CH3:16])[C:12]=3[CH:17]2[C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[CH3:36])[CH:26]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86707772HCID 86707772, compound

Product 1

HCID 86707771HCID 86707771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from example 16 (30 mg, 0.05 mmol) was dissolved in THF (0.7 mL) and TEA (10 mL, 0.07 mmol) was added. The reaction was cooled in an ice bath and acetyl chloride (5 mL, 0.06 mmol) was added. The cooling bath was removed and the reaction mixture allowed to stir at rt for 0.5 h. It was then diluted with EtOAc and brine and the aqueous phase extracted with EtOAc. The combined extracts were dried (Na2SO4) and concentrated. The remaining crude product was triturated with acetonitrile to give the title compound as a white solid, which was isolated by filtration and dried under reduced pressure. tR: 1.18/1.21 min (LC-MS 2); ESI-MS: 591.2/593.2 [M+H]+ (LC-MS 2).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customThe cooling bath was removed
  3. additionIt was then diluted with EtOAc and brine
  4. extractionthe aqueous phase extracted with EtOAc
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe remaining crude product was triturated with acetonitrile

Sources & evidence

ORD record
ord-74d0029362694c128ba02bd5928967ea
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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