Hydrochloric Acid → HCID 178473964, compound

HRID 1637954Notes

Reaction equation

HRID 1637954 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:16])(=[O:3])[CH3:2].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:23]([OH:24])[C:22]2[CH:26]=[CH:27][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:20][CH:21]=2)[C:5]1=[O:16])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 99664-(Trifluoromethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 28393291-Acetyl-5-nitroindolin-2-one

Product 1

HCID 178473964HCID 178473964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared by reacting 1-acetyl-5-nitro-2-indolinone with one equivalent of 4-trifluoromethyl-benzoic acid in dry DMF in the presence of 1 equivalent each of TBTU and HOBT and 5 equivalents of Huinig's base (20° C., 4 hours), stirring into dilute hydrochloric acid, filtering the precipitate, dissolving the precipitate in EtOac, drying the organic phase and evaporation in vacuo and purifying the evaporation residue by column chromatography on silica gel with CH2Cl2 /MeOH (10:1) as eluant.

Workup

  1. customPrepared
  2. filtrationfiltering the precipitate
  3. dissolutiondissolving the precipitate in EtOac
  4. customdrying
  5. customthe organic phase and evaporation in vacuo
  6. custompurifying the evaporation residue by column chromatography on silica gel with CH2Cl2 /MeOH (10:1) as eluant

Sources & evidence

ORD record
ord-ced276462a764a7a8b4fce8abba231b5
Source dataset
uspto-grants-2000_03
Patent number
US06043254

Reaction notes

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