1-Hydroxybenzotriazole → HCID 57901728, compound

HRID 1851558Notes

Reaction equation

HRID 1851558 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=1)[NH:7][C:6]([C:20](O)=[O:21])=[CH:5]2.[CH2:23]([S:30][C:31]([CH3:35])([CH3:34])[CH2:32][NH2:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C)C=O>[CH2:23]([S:30][C:31]([CH3:35])([CH3:34])[CH2:32][NH:33][C:20]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:10][C:9]=2[NH:11][S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])=[O:13])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 4235832-benzylsulfanyl-2-methylpropan-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901846HCID 57901846, compound

Product 1

HCID 57901728HCID 57901728, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-fluoro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.20 g), 2-(benzylthio)-2-methylpropylamine (0.13 g), 1H-1,2,3-benzotriazol-1-ol (0.11 g) and N,N-dimethylformamide (10 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.14 g) at 4° C., and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:8-4:6) to give the title compound (220 mg, crude yield 72%) as pale-purple crystals.

Workup

  1. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-049901f68fd84559952d3143015ecc98
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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