Chloroform → HCID 57433640, compound

HRID 2080679Notes

Reaction equation

HRID 2080679 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](Cl)=[O:15].C(Cl)(Cl)Cl.[NH2:21][C:22]1[CH:34]=[CH:33][C:32]([O:35][C:36]2[CH:37]=[N:38][C:39]([C:42]3[N:46]=[C:45]([CH3:47])[O:44][N:43]=3)=[CH:40][CH:41]=2)=[CH:31][C:23]=1[CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>O>[CH3:47][C:45]1[O:44][N:43]=[C:42]([C:39]2[N:38]=[CH:37][C:36]([O:35][C:32]3[CH:33]=[CH:34][C:22]([NH:21][C:14]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=4)=[O:15])=[C:23]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][C:26]4=[O:30])[CH:31]=3)=[CH:41][CH:40]=2)[N:46]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 57433639HCID 57433639, compound

Product 1

HCID 57433640HCID 57433640, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, 0.33 ml of triethylamine and 210 mg of picolinic acid chloride were added to a chloroform (2 ml) solution of 144 mg of 1-(2-amino-5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}benzyl)pyrrolidin-2-one, and stirred at room temperature for 1 hour. Water was added to it, extracted with chloroform, the organic layer was dried, the solvent was removed, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 2/8) to obtain 117 mg of N-{4-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyridine-2-carboxamide as a pale yellow solid.

Workup

  1. extractionextracted with chloroform
  2. customthe organic layer was dried
  3. customthe solvent was removed
  4. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 2/8)

Sources & evidence

ORD record
ord-4ac9386d70234febba36c5cd37b14d70
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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