Pyridine → HCID 67351296, compound

HRID 1672842Notes

Reaction equation

HRID 1672842 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:19]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:31]=1)[CH3:2].N1C=CC=CC=1.[C:38](Cl)(=[O:40])[CH3:39].C(=O)(O)[O-].[Na+]>ClCCl>[C:38]([N:28]1[CH2:29][CH2:30][CH:25]([O:24][C:20]2[CH:19]=[C:18]([N:15]3[CH2:14][C@H:13]4[N:9]([CH2:10][CH2:11][CH2:12]4)[C:8]4[N:31]=[C:4]([NH:3][CH2:1][CH3:2])[N:5]=[CH:6][C:7]=4[C:16]3=[O:17])[CH:23]=[CH:22][CH:21]=2)[CH2:26][CH2:27]1)(=[O:40])[CH3:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 67351083HCID 67351083, compound

Product 1

HCID 67351296HCID 67351296, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 147 (50.0 mg, 0.118 mmol) obtained in Example 147 was dissolved in dichloromethane (3 mL), cooled to 0° C., and stirred at 0° C. for 30 minutes after adding pyridine (0.0110 mL, 0.142 mmol) and acetyl chloride (0.0100 mL, 0.142 mmol). A saturated aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by preparative TLC to give the title compound (Compound 150) (54.2 mg, quantitative).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified by preparative TLC

Sources & evidence

ORD record
ord-6ae9aafd6182400283218dd485620c7f
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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