Chloroacetyl chloride → HCID 131732676, compound

HRID 1466036Notes

Reaction equation

HRID 1466036 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][NH:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:7][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:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH2:6][CH2:7]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 131732677HCID 131732677, compound

Product 1

HCID 131732676HCID 131732676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of tert-Butyl (2-{[(5-cyano-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)carbamate (184 mg, 0.58 mmol), chloro-acetyl chloride (85 mg, 0.76 mmol) and TEA (135 mg, 1.3 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 (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-d100fb04575c46ccafb627198ac26f5c
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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