Chloroacetyl chloride → HCID 131732673, compound

HRID 1466028Notes

Reaction equation

HRID 1466028 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][C:7]=1[C:8]#[N:9].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][N:12]([C:25](=[O:26])[CH2:24][Cl:23])[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 121005430HCID 121005430, compound

Product 1

HCID 131732673HCID 131732673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-Butyl (2-{[2-(3-bromo-4-cyanophenyl)ethyl]amino}ethyl)carbamate (30 mg, 0.081 mmol) and TEA (30 mg, 0.30 mmol) in DCM (1 mL) was added chloroacetyl chloride (10 mg, 0.089 mmol) to the mixture at 0° C. The mixture was stirred at RT for 0.5 hour. Then the residue was diluted with DCM (20 mL) washed with water (5 mL×2) dried over Na2SO4 and concentrated in vacuo to give the desired product. MS m/z: 444 [M+1]+.

Workup

  1. washwashed with water (5 mL×2)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69abcc328f2942309b8c01eedd6b2f64
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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