Acetyl chloride → HCID 22479264, compound

HRID 2182602Notes

Reaction equation

HRID 2182602 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[CH2:11][CH2:10][NH:9][CH2:8]3)=[CH:4][CH:3]=1.[C:28](Cl)(=[O:30])[CH3:29]>C1COCC1.CCN(C(C)C)C(C)C.CCOC(C)=O>[C:28]([N:9]1[CH2:8][C:7]2([CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Br:1])=[CH:3][CH:4]=3)[N:12]([C:13](=[O:25])[N:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:15]2=[O:16])[CH2:11][CH2:10]1)(=[O:30])[CH3:29]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 22479108HCID 22479108, compound

Product 1

HCID 22479264HCID 22479264, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,4,8-triazabicyclo[4.3.0]nonane-7,9-dione (0.062 g) in THF (2.5 mL) and DIEA (0.030 mL) was added acetyl chloride (0.015 mL). After 30 minutes, the reaction mixture was diluted with EtOAc and the solution washed with NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (Silica gel: CH2Cl2/MeOH: 99/1, Chromatotron) afforded the titled compound (0.046 g,). MS (m/z) 510 (MH+). mp 89.6° C.

Workup

  1. washthe solution washed with NaHCO3, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (Silica gel: CH2Cl2/MeOH: 99/1, Chromatotron)

Sources & evidence

ORD record
ord-0d498a5a2b484e638a8e99f306adfcb4
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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