Acetyl chloride → HCID 21939446, compound

HRID 1242810Notes

Reaction equation

HRID 1242810 reaction equation
[CH2:1]([C:3]1[S:25][C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([CH:19]4[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]4)=[O:18])[CH2:13][CH2:12]3)[C:5]=2[CH:4]=1)[CH3:2].[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl.C(N(C(C)C)CC)(C)C>[CH2:1]([C:3]1[S:25][C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([CH:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:26](=[O:28])[CH3:27])[CH2:20]4)=[O:18])[CH2:13][CH2:12]3)[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 21939442HCID 21939442, compound

Product 1

HCID 21939446HCID 21939446, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

[4-(6-Ethyl-thieno[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-piperidin-3-yl-methanone (Example 294, 17.0 mg) was dissolved in methylene chloride (1.00 mL) and diisopropylethylamine (12.4 μL). Acetylchloride (3.7 μL) was added and the reaction was stirred at room temperature for 30 minutes. The reaction was applied to silica gel and the product was isolated by eluting from 0% to 4% methanol/methylene chloride over 45 minutes then 10% methanol/methylene chloride for 15 minutes. Yield=53%, ES-MS: (M+H)+ 402

Workup

  1. customthe product was isolated
  2. washby eluting from 0% to 4% methanol/methylene chloride over 45 minutes
  3. wait10% methanol/methylene chloride for 15 minutes

Sources & evidence

ORD record
ord-39a18bac979046e59769ebdc94793db4
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

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