Chloroacetaldehyde → HCID 58382132, compound

HRID 1628113Notes

Reaction equation

HRID 1628113 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[C:10]([CH2:11][CH3:12])=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=3)[N:8]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:5]2=[N:6][CH:7]=1.Cl[CH2:31][CH:32]=O>CCO>[CH2:11]([C:10]1[C:4]2[N:3]3[CH:31]=[CH:32][N:1]=[C:2]3[CH:7]=[N:6][C:5]=2[N:8]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[C:9]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=1)[CH3:12]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 58382020HCID 58382020, compound

Product 1

HCID 58382132HCID 58382132, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-(2-Amino-7-ethyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl)ethanone (0.217 g, 0.529 mmol) in EtOH (5 mL) was treated with 2-chloroacetaldehyde (˜50 wt % solution in water, 0.100 g, 0.634 mmol). The mixture was heated to about 80° C. for about 2 h then cooled to rt and concentrated under reduced pressure. The material was purified by on a 10 gram silica column with EtOAc then 9:1 DCM/MeOH as eluents to give 1-(4-(1-ethyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)ethanone (0.12 g, 52%): LC/MS (Table 2, Method a) Rt=3.06 min; MS m/z 435 (M+H)+.

Workup

  1. temperaturethen cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customThe material was purified by on a 10 gram silica column with EtOAc

Sources & evidence

ORD record
ord-4c94404edc314dcd932c6ea13b57b80f
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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