Triethylamine → 1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one

HRID 2189949Notes

Reaction equation

HRID 2189949 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:11][N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3].C(N(CC)CC)C.[C:33](Cl)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]([C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 866048312-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

Product 1

HCID 866048381-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (100 mg, 0.278 mmol, Example 5, Step B) was weighed into a flask and dissolved in 5.0 mL of CH2Cl2. Triethylamine (0.0581 ml, 0.417 mmol) was then added, followed by pivaloyl chloride (40.2 mg, 0.333 mmol). The reaction was then allowed to slowly warm to ambient temperature over 12 hours. The reaction was concentrated and purified by flash column chromatography (10% ethyl acetate/Hexanes) affording the desired product (100 mg, 81%).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by flash column chromatography (10% ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-23dbde65776d427394812f8f4b660840
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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