Acetyl chloride → HCID 178474363, compound

HRID 1378442Notes

Reaction equation

HRID 1378442 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:13][C:14]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:17][CH2:16][CH2:15]2)=[N:10][C:11]#[N:12])[CH:5]=[N:6][CH:7]=1.[C:24](Cl)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([NH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:13][C:14]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:17][CH2:16][CH2:15]2)=[N:10][C:11]#[N:12])[CH:5]=[N:6][CH:7]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178512302HCID 178512302, compound

Product 1

HCID 178474363HCID 178474363, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of the product from Example 3 (0.87 g, 0.0028 mol) in pyridine (10 ml), was cooled under nitrogen in an ice bath and treated with acetyl chloride (0.22 ml, 0.0031 mol). The mixture was kept in the ice bath for 1 hour and at ambient temperature for 20 hours. It was then concentrated in vacuo. The residue was mixed with saturated NaHCO3 and extracted with CHcl3. The extract was concentrated in vacuo and the residue was chromatographed on silica gel with 5% MeOH-0.25% NH4OH--CHcl3. The product was crystallized from MeOH-EtOAc to give 0.343 g, mp 208°-209° C. and 0.0813 g, mp 207°-208° C. of the titled product.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. additionThe residue was mixed with saturated NaHCO3
  3. extractionextracted with CHcl3
  4. concentrationThe extract was concentrated in vacuo
  5. customthe residue was chromatographed on silica gel with 5% MeOH-0.25% NH4OH--CHcl3
  6. customThe product was crystallized from MeOH-EtOAc

Sources & evidence

ORD record
ord-048baf64f4df4a8eabb4b27b35fd76e4
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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