Pyridine → HCID 178456585, compound

HRID 892112Notes

Reaction equation

HRID 892112 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[NH:17][C:16]3[C:15]4=[N:18][C@H:19]([CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][N:14]4[C:13](=[O:28])[N:12]([CH2:29][CH2:30][CH3:31])[C:11]=3[N:10]=2)[CH2:5][CH2:4]1.[C:32](OC(=O)C)(=[O:34])[CH3:33].N1C=CC=CC=1.C(=O)([O-])O.[Na+].C(Cl)[Cl:51]>>[ClH:51].[C:32]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]2[NH:17][C:16]3[C:15]4=[N:18][C@H:19]([CH2:21][C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:20][N:14]4[C:13](=[O:28])[N:12]([CH2:29][CH2:30][CH3:31])[C:11]=3[N:10]=2)[CH2:7][CH2:8]1)(=[O:34])[CH3:33]

Participants

6

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178456584HCID 178456584, compound

Product 1

HCID 178456585HCID 178456585, compound

Procedure

Compound 62 (50 mg, 0.119 mmol) obtained in Example 62 was dissolved in methylene chloride (500 μL), to the solution were added acetic anhydride (11 μL, 0.119 mmol, 1.0 equivalent) and pyridine (10 μL, 0.120 mmol, 1.0 equivalent), and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 98:2) to obtain the title compound in the free form (50 mg). The free compound was converted into hydrochloride with a 4 mol/L solution of hydrogen chloride in dioxane and the product was recrystallized from ethanol to obtain the title compound (51 mg, 86%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 98:2)

Sources & evidence

ORD record
ord-42cac8a6c97d4160b84ef6b157b499f0
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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