Acetyl chloride → HCID 178474794, compound

HRID 16688Notes

Reaction equation

HRID 16688 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:34])[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([NH:14][C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[O:17][C:16]=2[C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=2)=[O:25])=[O:13])[CH2:8][CH2:7]1.C(N(CC)CC)C.[C:42](Cl)(=[O:44])[CH3:43].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:42]([NH:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:34])[C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]([NH:14][C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[O:17][C:16]=2[C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=2)=[O:25])=[O:13])[CH2:10][CH2:11]1)(=[O:44])[CH3:43]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178483799HCID 178483799, compound

Product 1

HCID 178474794HCID 178474794, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-[({Trans-4-[(3-aminopropyl)(methyl)amino]cyclohexyl}-carbonyl)amino]-N-(5-chloropyridin-2-yl)furo[3,2-b]pyridine-2-carboxamide (113 mg) obtained in Example 121 and triethylamine (65 μl) are dissolved in chloroform (5 ml), and thereto is added acetyl chloride (25 μl) under ice-cooling. The mixture is warmed to room temperature and stirred for 1 hour. To the reaction solution is poured saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed successively with water and saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1). The resulting solid is suspended in n-hexane-diisopropyl ether, and collected by filtration to give the title compound (90 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed successively with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-231f1469e8774c6289990276e490ee84
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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