Ethyl 2-chloroethanecarboximidate hydrochloride → HCID 66958631, compound

HRID 1364079Notes

Reaction equation

HRID 1364079 reaction equation
[NH2:1][C:2]1[C:3]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:4][C:5]([CH3:20])=[C:6]([CH3:19])[C:7]=1[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].Cl.[Cl:29][CH2:30][C:31](=N)OCC>C(Cl)(Cl)Cl>[Cl:29][CH2:30][C:31]1[N:8]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7]2[C:6]([CH3:19])=[C:5]([CH3:20])[N:4]=[C:3]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochloride2×HCID 21973843Tert-butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate

Product 1

HCID 66958631HCID 66958631, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate (17.9 g, 48.1 mmol), prepared as described in U.S. Pat. No. 6,545,016 Example 23, Parts A through C, was dissolved in chloroform (250 mL). Ethyl 2-chloroacetimidate hydrochloride (15.2 g, 96 mmol) was added to the solution and the reaction mixture was stirred at 60° C. for 5 hours. Additional ethyl 2-chloroacetimidate hydrochloride (1.9 g) was added to the reaction mixture and stirred for 0.5 hours. The reaction mixture was cooled and filtered. The filtrate was diluted with chloroform (250 mL), washed with brine (2×300 mL), and the layers were separated. The combined organics were dried over magnesium sulfate, filtered with CELITE filter aid, and concentrated under reduced pressure. The material was recrystallized and filtered from acetonitrile to yield 13.28 g of tert-butyl 2-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]ethylcarbamate as a white solid.

Workup

  1. stirringstirred for 0.5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. additionThe filtrate was diluted with chloroform (250 mL)
  5. washwashed with brine (2×300 mL)
  6. customthe layers were separated
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered with CELITE
  9. filtrationfilter aid
  10. concentrationconcentrated under reduced pressure
  11. customThe material was recrystallized
  12. filtrationfiltered from acetonitrile

Sources & evidence

ORD record
ord-2ddba8c4e07d44a48aeae357ba33f602
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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