Sodium Bicarbonate → HCID 10099191, compound

HRID 1173908Notes

Reaction equation

HRID 1173908 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.[CH2:31]([O:33][C:34]1[C:35]([CH:40]=O)=[N:36][CH:37]=[CH:38][CH:39]=1)[CH3:32].[C:42]([BH3-])#[N:43].[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:43]([CH2:42][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:23][CH:24]=[CH:25][N:26]=3)[CH2:40][C:35]3[C:34]([O:33][CH2:31][CH3:32])=[CH:39][CH:38]=[CH:37][N:36]=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 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 12908934HCID 12908934, compoundHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

Product 1

HCID 10099191HCID 10099191, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (104 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and added with 3-ethoxy-2-pyridine aldehyde (74.7 mg) synthesized by the method described in Marsais, F et al, Synthesis, 235 (1982), followed by the addition of sodium cyanoborohydride (46.6 mg). After that, the reaction solution was adjusted to about pH 5 with acetic acid and then stirred at room temperature for 65 hours. The reaction solution was added with a saturated aqueous sodium bicarbonate solution and then extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off. The resulting crude product was purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (132 mg) of the subject compound as a white solid.

Workup

  1. customsynthesized by the method
  2. customdescribed in Marsais, F et al, Synthesis, 235 (1982)
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customThe resulting crude product was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-d90233dff12941858178109ea2b81c0c
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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