1-Methyl-2-imidazolecarboxaldehyde → 6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

HRID 2080776Notes

Reaction equation

HRID 2080776 reaction equation
[CH2:1]([N:4]([CH2:29][CH2:30][CH3:31])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][CH2:22][C:23]3[NH:24][CH:25]=[CH:26][N:27]=3)[CH2:16][N:15]2[CH:28]=1)=[O:11])[CH2:2][CH3:3].[CH3:32][N:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH2:29]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][N:21]([CH2:22][C:23]3[NH:24][CH:25]=[CH:26][N:27]=3)[CH2:38][C:34]3[N:33]([CH3:32])[CH:37]=[CH:36][N:35]=3)[CH2:16][N:15]2[CH:28]=1)=[O:11])[CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 231554046-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

Product 1

HCID 583458086-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amideYield 92.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (19.6 mg) obtained in Example 19-4 was dissolved in methanol (2.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (6.2 mg) and sodium cyanoborohydride (5.9 mg). The solution was adjusted to pH 4 with acetic acid and stirred at room temperature for 3 hours. The resultant was added with a saturated sodium hydrogen carbonate aqueous solution to stop the reaction and subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (22.0 mg) of the subject compound as a white solid.

Workup

  1. customthe reaction
  2. extractionsubjected to extraction with chloroform
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline solution and dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-ac480886f4264a4b8cf7245e1df48ddc
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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