Chloroacetyl chloride → HCID 131732674, compound

HRID 1466032Notes

Reaction equation

HRID 1466032 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:8][CH2:7][CH2:6]2)#[N:2].[Cl:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[Cl:25][CH2:26][C:27]([N:14]([CH2:13][CH:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1)[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:28]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 131732675HCID 131732675, compound

Product 1

HCID 131732674HCID 131732674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of tert-Butyl (2-{[(6-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate (110 mg, 0.334 mmol), chloroacetyl chloride (42 mg, 0.37 mmol) and TEA (135 mg, 1.34 mmol) in 20 mL DCM was stirred at RT for 12 hours. The mixture was diluted with 50 mL DCM and then washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified via prep-TLC (EtOAc/Petroleum Ether=1:1) to give the title compound. MS m/z: 406 [M+1]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified via prep-TLC (EtOAc/Petroleum Ether=1:1)

Sources & evidence

ORD record
ord-8d0fb58ef5974b61ba473815fba4fcd3
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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