Sodium Hydroxide → HCID 10438338, compound

HRID 1173946Notes

Reaction equation

HRID 1173946 reaction equation
C(N(CCC)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]3[NH:23][CH:24]=[CH:25][N:26]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)CC.[CH3:31][O:32][CH2:33][O:34][CH2:35][CH2:36][N:37]1[CH:41]=[CH:40][N:39]=[C:38]1[CH:42]=O.[C:44]([BH3-])#[N:45].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:45]([CH2:44][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]([CH2:21][C:22]3[NH:26][CH:25]=[CH:24][N:23]=3)[CH2:42][C:38]3[N:37]([CH2:36][CH2:35][O:34][CH2:33][O:32][CH3:31])[CH:41]=[CH:40][N:39]=3)=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamideHCID 23079305HCID 23079305, compound

Product 1

HCID 10438338HCID 10438338, compoundYield 139.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (120 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml). The solution was added with the compound (73.0 mg) obtained in Example 92-2 and sodium cyanoborohydride (18.0 mg) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 2 days. After completion of the reaction, the reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution, followed by separation/extraction with chloroform. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (121 mg) as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by separation/extraction with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-8355e55971384500a71c3ccb1b6ce663
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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