Chloroacetyl chloride → HCID 131732669, compound

HRID 1466019Notes

Reaction equation

HRID 1466019 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[Cl:23][CH2:24][C:25]([N:12]([CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:1]#[N:2])[CH:4]=1)[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:26]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 121005435HCID 121005435, compound

Product 1

HCID 131732669HCID 131732669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-Butyl (2-{[2-(3-cyano-4-fluorophenyl)ethyl]amino}ethyl)carbamate (0.9 g, 3.1 mmol) and TEA (0.4 g, 3.7 mmol) in 10 mL of anhydrous DCM was added chloroacetyl chloride (0.4 g, 3.7 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 1 h, and then the solvent was evaporated. The residue was partitioned between EtOAc and water. The organic layer was dried and evaporated. The residue was purified with prep-TLC to give tert-Butyl (2-{(chloroacetyl) [2-(3-cyano-4-fluorophenyl)ethyl]amino}ethyl)carbamate.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between EtOAc and water
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-767c2f2f618045ec889f2d35dda51c08
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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