Triethylamine → HCID 86722650, compound

HRID 1480416Notes

Reaction equation

HRID 1480416 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.[C:32]([O:36][C:37](=[O:42])[NH:38][CH2:39][CH2:40]Br)([CH3:35])([CH3:34])[CH3:33]>CC#N.CCOC(C)=O>[C:32]([O:36][C:37]([NH:38][CH2:39][CH2:40][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[O:8])[CH2:2][CH2:3]1)=[O:42])([CH3:35])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate2×HCID 59474105HCID 59474105, compound

Product 1

HCID 86722650HCID 86722650, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3,5-Dichlorobenzyl piperazine-1-carboxylate (Example 26, step 2) (3.466 mg, 11.99 mmol), potassium carbonate (4.97 g, 36 mmol) and triethlyamine (5.01 ml, 36 mmol) were suspended in MeCN (60 ml). tert-Butyl(2-bromoethyl)carbamate (3.49 g, 15.58 mmol) was added and the reaction mixture was refluxed for 18 hrs at 80° C. A further portion of tert-butyl(2-bromoethyl)carbamate (1.05 g, 4.69 mmol) was added and heating continued at 80° C. for 3 hrs. After cooling to RT, the reaction mixture was diluted with EtOAc and filtered. The organic portion was evaporated under reduced pressure. The crude product was solubilised in EtOAc and washed with 2M NaOH. The organic portion was dried over MgSO4 (anh) filtered and evaporated under reduced pressure. Purification by chromatography on silica using a gradient solvent system of DCM to 10% MeOH with ammonia in DCM afforded product fractions that were concentrated to give the title compound;

Workup

  1. temperatureheating
  2. temperatureAfter cooling to RT
  3. filtrationfiltered
  4. customThe organic portion was evaporated under reduced pressure
  5. washwashed with 2M NaOH
  6. dry with materialThe organic portion was dried over MgSO4 (anh)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customPurification by chromatography on silica using a gradient solvent system of DCM to 10% MeOH with ammonia in DCM afforded product fractions that
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-d785b5c8862c48b7a6899fada045ba3d
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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