Aniline → HCID 178466771, compound

HRID 333640Notes

Reaction equation

HRID 333640 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12](=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]([CH3:27])([CH3:26])[NH:17]2)[C:13](O)=[O:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:28]1([NH2:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.ClCCl.C(N(CC)CC)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]=[N:11][C:12](=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]([CH3:26])([CH3:27])[NH:17]2)[C:13]([NH:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:14])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178466773HCID 178466773, compound

Product 1

HCID 178466771HCID 178466771, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

(4-acetyl-phenylazo)-(3,3-dimethyl-3,4-dihydro-2H-isoquinoline-1-ylidene)-acetic acid, phenylamine, HOBt (Advanced ChemTech Corp., USA) and triethylamine are dissolved in DMF, a dichloromethane solution of HBTU (Advanced ChemTech Corp., USA) is added, and then the mixture is stirred at room temperature. The mixture is washed with the saturated aqueous sodium chloride solution and a 5% aqueous sodium hydrogen carbonate solution. The reaction product is dried with anhydrous sodium sulfate and filtered and, then, the solvent is removed by reducing the pressure. The residue containing the reaction product is purified by column chromatography to obtain the title compound.

Workup

  1. washThe mixture is washed with the saturated aqueous sodium chloride solution
  2. dry with materialThe reaction product is dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed
  5. additionThe residue containing the reaction product
  6. customis purified by column chromatography

Sources & evidence

ORD record
ord-b6915a19246f4f1491ec4c12a2920335
Source dataset
uspto-grants-2014_11
Patent number
US08883504B2

Reaction notes

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