Cyanogen Bromide → HCID 59510519, compound

HRID 602294Notes

Reaction equation

HRID 602294 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH3:28])[CH:3]=1.[N:29]#[C:30]Br>C(Cl)Cl>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([C:30]#[N:29])[CH2:21][CH2:22]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH3:28])[CH:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 59510469HCID 59510469, compound

Product 1

HCID 59510519HCID 59510519, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-5-chloro-2-ethoxy-N-[{4-(4-piperidinylmethyl)-2-morpholinyl}-methyl]benzamide (Example 22) (1.0 g) and TEA (0.41 ml) in methylene chloride (10 ml) was added cyanogen bromide (0.27 g) at room temperature, and then the mixture was stirred for 4 hours, washed with water, then brine and dried over anhydrous magnesium sulfate. Then, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (0.7 g) as a white solid. Melting point 197° C. (degradation, recrystallized from E)

Workup

  1. washwashed with water
  2. dry with materialbrine and dried over anhydrous magnesium sulfate
  3. customThen, the solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-5484bf5c39ad4bf295ea49a01cdee019
Source dataset
uspto-grants-2011_03
Patent number
US07906510B2

Reaction notes

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