Chloroacetyl chloride → tert-Butyl (2-{(chloroacetyl)[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate

HRID 1466042Notes

Reaction equation

HRID 1466042 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][NH:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:6]2)#[N:2].[Cl:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[Cl:24][CH2:25][C:26]([N:13]([CH2:12][CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH2:8]1)[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:27]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 131732678tert-Butyl (2-{[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate

Product 1

HCID 131732679tert-Butyl (2-{(chloroacetyl)[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of tert-Butyl (2-{[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate (460 mg, 1.5 mmol), chloro-acetyl chloride (180 mg, 1.6 mmol) and TEA (590 mg, 5.8 mmol) in 30 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 (EA/PE=1:1) to give the title compound. MS m/z: 392 [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 (EA/PE=1:1)

Sources & evidence

ORD record
ord-5863869fbd134e90bc11676fbc402dc8
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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