Sodium Bicarbonate → N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(5-methylpyrazine-2-ylmethyl)-amino]-methyl}-benzamide

HRID 348669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348669
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][C:32]1[N:33]=[CH:34][C:35]([CH:38]=O)=[N:36][CH:37]=1.[C:40]([BH3-])#[N:41].[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:41]([CH2:40][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)[CH2:38][C:35]3[CH:34]=[N:33][C:32]([CH3:31])=[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]

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 136249775-Methylpyrazine-2-carboxaldehydeHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

Produkt 1

HCID 10369575N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(5-methylpyrazine-2-ylmethyl)-amino]-methyl}-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound (82.2 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and added with the compound (35.9 mg) obtained in Example 73-1, followed by the addition of sodium cyanoborohydride (36.9 mg). Then, the reaction solution was adjusted to about pH 5 with acetic acid, followed by stirring at room temperature for 16 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 treated with hydrochloric acid, thereby obtaining hydrochloride (84.0 mg) of the subject compound as a pale-yellow solid.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customThe resulting crude product was purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-419aab356afa4ca4991423f0ea59a318
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176227B2

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