Dimethylformamide → HCID 178453113, compound

HRID 1628198Notes

Reaction equation

HRID 1628198 reaction equation
F[C:2](=[O:25])[C@@H:3]([N:11]([CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=[C:28]([C:32]2O[C:35]([NH2:37])=[N:34][N:33]=2)C=1.C([N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])C.C[N:46](C=O)C>>[O:25]=[C:2]([NH:46][C:35]1[NH:37][C:32]([C:28]2[CH:42]=[CH:41][N:40]=[CH:43][CH:44]=2)=[N:33][N:34]=1)[C@@H:3]([N:11]([CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 219401,3,4-Oxadiazole, 2-amino-5-(3-pyridyl)-HCID 86664819HCID 86664819, compound

Product 1

HCID 178453113HCID 178453113, compoundYield 43%

Procedure

To a rt solution of 2.D (267 mg, 0.73 mmol) in DMF (2.5 mL) under N2 was added 5-(pyridin-3-yl)-1,3,4-oxadiazol-2-amine (available from Chemical Block Ltd.) (143 mg, 0.88 mmol) followed by triethylamine (available from Alfa Aesar) (255 μl, 1.82 mmol). After stirring at rt for overnight, the reaction was quenched with saturated NaHCO3, diluted with water, and extracted with EtOAc. After removal of organic solvent, purification by flash chromatography on silica gel using 0-10% MeOH/CH2Cl2 for elution to give 2.E as pale yellow syrup (159 mg, 43%).

Workup

  1. customthe reaction was quenched with saturated NaHCO3
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. customAfter removal of organic solvent, purification by flash chromatography on silica gel using 0-10% MeOH/CH2Cl2
  5. washfor elution

Sources & evidence

ORD record
ord-0418ad97867b44728d9bc3613d61d596
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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