Water → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine

HRID 634222Notes

Reaction equation

HRID 634222 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11](O)=[O:12])[CH:9]=2)[N:4]([S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1.[C:24]1([C:30]([NH:33][C:34]([NH:36][NH2:37])=S)([CH3:32])[CH3:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.C(N=C=NCCCN(C)C)C.O>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:12][C:34]([NH:33][C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([CH3:32])[CH3:31])=[N:36][N:37]=3)[CH:9]=2)[N:4]([S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 133883954-(2-Phenylpropan-2-yl)thiosemicarbazideHCID 683285993-iodo-1-tosyl-1H-indole-5-carboxylic acid

Product 1

HCID 683287405-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amineYield 22.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-iodo-1-tosyl-1H-indole-5-carboxylic acid (1.330 g, 3.01 mmol), N-(2-phenylpropan-2-yl)hydrazinecarbothioamide (0.631 g, 3.01 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.156 g, 6.03 mmol) (Sigma-Aldrich) in DMF (5.0 mL) was heated at 80° C. for 2 h. The solution was cooled to RT. Water (precipitate formed), EtOAc and Celite were added, and the solids were removed by filtration and washed with EtOAc (3×). The organic layer was evaporated to reduce solvent volume. The aqueous layer was then extracted with EtOAc (2×50 mL). The combined organic layers were concentrated in vacuo, and the crude material was purified by flash chromatography (20-100% EtOAc in Hex) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (408.1 mg, 0.682 mmol, 22.62%). MS (ESI, pos. ion) m/z: 599.0 (M+1).

Workup

  1. customthe solids were removed by filtration
  2. washwashed with EtOAc (3×)
  3. customThe organic layer was evaporated
  4. extractionThe aqueous layer was then extracted with EtOAc (2×50 mL)
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. customthe crude material was purified by flash chromatography (20-100% EtOAc in Hex)

Sources & evidence

ORD record
ord-3c93b3d298844f9b907657f1b18264ab
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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