Aniline → HCID 57901581, compound

HRID 1851463Notes

Reaction equation

HRID 1851463 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:20]=2[NH:19][C:18]([C:21]([OH:23])=O)=[CH:17]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(OCC)(=O)C.CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:20]=2[NH:19][C:18]([C:21]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])=[CH:17]3)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57901852HCID 57901852, compound

Product 1

HCID 57901581HCID 57901581, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-{[(4-methylphenyl)sulfonyl]amino}-1H-indole-2-carboxylic acid (110 mg), aniline (38 μL), ethyldiisopropylamine (0.29 mL), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (180 mg) and N,N-dimethylformamide (4 mL) was stirred at 60° C. for 7 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, water 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=1:1), and the obtained crystals were washed with ethyl acetate-hexane to give the title compound (75 mg, yield 55%) as colorless crystals. melting point 247-248° C.

Workup

  1. washwashed with aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washthe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-cce287e1e67d4518be276fd2efdd2773
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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