Cyanogen Bromide → Anagrelide Hydrochloride

HRID 614902Notes

Reaction equation

HRID 614902 reaction equation
[N:1]#[C:2]Br.C(O[C:7](=[O:20])[CH2:8][NH:9][CH2:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([Cl:18])[C:12]=1[Cl:19])C>COCCO>[ClH:18].[Cl:19][C:12]1[C:13]([Cl:18])=[CH:14][CH:15]=[C:16]2[C:11]=1[CH2:10][N:9]1[CH2:8][C:7](=[O:20])[NH:1][C:2]1=[N:17]2

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 9814186Ethyl 2-((6-amino-2,3-dichlorobenzyl)amino)acetate

Product 1

HCID 135413494Anagrelide HydrochlorideYield 31%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent2×

Procedure

A solution of cyanogen bromide (3.2 g, 0.030 mol) in 100 ml. 2-methoxyethanol was added to a solution of N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester (8.2 g, 0.030 mol) in 250 ml. 2-methoxyethanol. The solution was stirred at room temperature for 1 hour, heated at reflux for 22 hours, and cooled. The precipitate was filtered off, washed with ether and air dried to give 3.11 gms. of the crude title product (31% yield as the hydrobromide salt). Recrystallization from ethanolic HCl gave the pure title product in 71% recovery (22% overall yield); m.p. >250°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 22 hours
  3. temperaturecooled
  4. filtrationThe precipitate was filtered off
  5. washwashed with ether and air
  6. customdried
  7. customto give 3.11 gms
  8. customRecrystallization from ethanolic HCl

Sources & evidence

ORD record
ord-56be5e26d86e45a2bf84af2e8d3aedad
Source dataset
uspto-grants-1979_03
Patent number
US04146718

Reaction notes

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