Dimethylacetamide → N-Methyl-N-(2-{5-[2-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-yl}-1H-indol-7-yl)thiophene-2-sulfonamide

HRID 1851554Notes

Reaction equation

HRID 1851554 reaction equation
[NH:1]([C:3](=[O:30])[CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]([CH3:29])[S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[N:8][CH:7]=1)[NH2:2].[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32].CN(C)C(=O)C>O>[CH3:29][N:20]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:9]1[S:10][C:6]([CH2:5][CH2:4][C:3]3[O:30][C:31](=[O:32])[NH:2][N:1]=3)=[CH:7][N:8]=1)=[CH:19]2)[S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 682631,1'-CarbonyldiimidazoleHCID 57901791N-{2-[5-(3-hydrazino-3-oxopropyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

Product 1

HCID 57901682N-Methyl-N-(2-{5-[2-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-yl}-1H-indol-7-yl)thiophene-2-sulfonamideYield 65.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-{2-[5-(3-hydrazino-3-oxopropyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide (0.29 g), 1,1′-carbonylbis-1H-imidazole (0.22 g) and N,N-dimethylacetamide (15 mL) was stirred at room temperature for 2 hr. Water was added to the reaction mixture and the resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (0.20 g, yield 65%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate. melting point 255-256° C.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-b1ddb83b45fa4b16b00d9ab47d8f1d6c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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