Dimethylamine → HCID 69059990, compound

HRID 860105Notes

Reaction equation

HRID 860105 reaction equation
[CH3:1][NH:2][CH3:3].O1CCCC1.[CH3:9][N:10]1[N:14]=[C:13]2[CH:15]=[CH:16][C:17]([C:19]3[N:20]=[C:21]([CH:31]=O)[NH:22][C:23]=3[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[CH:18][C:12]2=[N:11]1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O.C(O)(=O)C>[CH3:1][N:2]([CH3:3])[CH2:31][C:21]1[NH:22][C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)=[C:19]([C:17]2[CH:16]=[CH:15][C:13]3=[N:14][N:10]([CH3:9])[N:11]=[C:12]3[CH:18]=2)[N:20]=1

Participants

9

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86592586HCID 86592586, compound

Product 1

HCID 69059990HCID 69059990, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2M solution of dimethylamine in tetrahydrofuran (189 μl, 0.378 mmol) was dissolved in 2 ml anhydrous methanol. Glacial acetic acid was added until approximately pH 4. 4-(2-methyl-2H-benzotriazol-5-yl)-5-(6-methyl-pyridin-2-yl)-1H-imidazole-2-carbaldehyde (20 mg, 0.063 mmol) was added and the reaction stirred at room temperature for 3 hours. Sodium cyanoborohydride (6 mg, 0.095 mmol) was added and the reaction stirred at room temperature overnight. 1M solution of sodium hydroxide in water was added until the reaction pH was 8 and the organic solvent was then removed by rotary evaporation. The residue was dissolved in water and extracted three times with chloroform. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to dryness. The residue was purified on Biotage Flash 12S silica gel column using chloroform/methanol gradient system (95:5 to 80:20, respectively) as eluent to afford dimethyl-[4-(2-methyl-2H-benzotriazol-5-yl)-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-ylmethyl]-amine (6 mg, 28% yield). HPLC tR=3.29 min, LC-MS=348 (M+1).

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. customthe organic solvent was then removed by rotary evaporation
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with chloroform
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified on Biotage Flash 12S silica gel column

Sources & evidence

ORD record
ord-bc23e685bdf34f09a3f441ced3b4b447
Source dataset
uspto-grants-2006_12
Patent number
US07153872B2

Reaction notes

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