Methylamine → HCID 178485801, compound

HRID 333638Notes

Reaction equation

HRID 333638 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].CN.C1C=CC2N(O)N=[N:36][C:34]=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]([CH3:27])([CH3:26])[NH:17]2)[C:13]([NH:36][CH3:34])=[O:14])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178466773HCID 178466773, compound

Product 1

HCID 178485801HCID 178485801, 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, methylamine, HOBt (Advanced ChemTech Corp., USA) and triethylamine are dissolved in DMF, and a dichloromethane solution of HBTU (Advanced ChemTech Corp., USA) is added thereto. The mixture is then stirred at room temperature. The mixture is washed with a 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 a 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-41d6b79ac40242ae996a89874727140c
Source dataset
uspto-grants-2014_11
Patent number
US08883504B2

Reaction notes

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