Acetyl chloride → HCID 68863946, compound

HRID 494140Notes

Reaction equation

HRID 494140 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]3[CH2:22][CH2:21][N:20]([CH3:23])[C:19](=[O:24])[C:9]3=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[C:5](=[O:25])[N:4]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[C:43](Cl)(=[O:45])[CH3:44]>C(Cl)(Cl)Cl>[CH2:12]([O:11][C:10]1[C:6]2[C:5](=[O:25])[N:4]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[N:3]=[C:2]([NH:1][C:43](=[O:45])[CH3:44])[C:7]=2[N:8]2[CH2:22][CH2:21][N:20]([CH3:23])[C:19](=[O:24])[C:9]=12)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68865270HCID 68865270, compound

Product 1

HCID 68863946HCID 68863946, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 4-amino-2-(4-fluorobenzyl)-10-benzyloxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (21 mg, 47 μmol) and diisopropylethylamine (10 μL, 56 μmol) in anhydrous chloroform (2 mL), acetyl chloride (8 μL, 104 μmol) was added. The mixture was stirred at room temperature for 30 minutes and concentrated under vacuum. The intermediate bisacetylated product was dissolved in methanol, stirred at room temperature overnight, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel. Collection and concentration of appropriate fractions provided the title monoacetylated product.

Workup

  1. additionwas added
  2. concentrationconcentrated under vacuum
  3. dissolutionThe intermediate bisacetylated product was dissolved in methanol
  4. stirringstirred at room temperature overnight
  5. concentrationconcentrated under vacuum
  6. customCollection and concentration of appropriate fractions
  7. customprovided the title monoacetylated product

Sources & evidence

ORD record
ord-00fc0683c1ec4863b89db35df620e4b9
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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