Formaldehyde → HCID 23155417, compound

HRID 1173899Notes

Reaction equation

HRID 1173899 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C=O.[C:36]([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][N:20]([CH3:36])[CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:26][CH2:27][CH3:28])[CH2:29][CH2:30][CH3:31])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 10253296HCID 10253296, compound

Product 1

HCID 23155417HCID 23155417, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (150.7 mg) obtained in Example 25-5 was dissolved in methanol (3.0 ml). Then, a 36% formaldehyde aqueous solution (manufactured by Kanto Kagaku) (50 μl) and sodium cyanoborohydride (36.2 mg) were added to the solution in this order. After the reaction solution was adjusted to pH 5 with acetic acid, the solution was stirred at room temperature for 17 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then extracted with chloroform. Subsequently, the organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After the solvent had been distilled off, the residue obtained was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining hydrochloride (126.2 mg) of the subjected compound as a white solid.

Workup

  1. extractionextracted with chloroform
  2. washSubsequently, the organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter the solvent had been distilled off
  5. customthe residue obtained
  6. customwas purified through silica gel column chromatography (chloroform/ethyl acetate)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-7d740585bf0a4aebb8dc7e4cda007b2b
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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