Acetyl chloride → HCID 22479264, compound

HRID 1392170Notes

Reaction equation

HRID 1392170 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-b10b490ced164cfaad8be3207d51b441
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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