Isoquinoline-1-carboxylic acid → HCID 178481697, compound

HRID 33221

Reaction equation

HRID 33221 reaction equation
OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:23][NH:24][C:25](=[S:28])[NH:26][NH2:27].[C:29]1([C:39](O)=O)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][N:30]=1>CN(C)C=O.C(N(CC)CC)C>[C:29]1([C:39]2[N:24]([CH3:23])[C:25]([SH:28])=[N:26][N:27]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][N:30]=1

Participants

7

Reactant 4

HCID 68092Isoquinoline-1-carboxylic acidHCID 2723853N-MethylhydrazinecarbothioamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 178481697HCID 178481697, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Hydroxybenzotriazole (0.078 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) and triethylamine were added successively to a cooled solution (0° C.) of 4-methyl-3-thiosemicarbazide (0.061 g) and 1-isoquinoline carboxylic acid (0.10 g) in dimethylformamide (3 ml). Following addition the cooling bath was removed and the mixture was stirred at room temperature over night and then the reaction mixture was evaporated to dryness. To the residue was added sodium hydroxide solution (0.5 M, 5 ml) and the mixture was stirred at 80° C. for 3 h. The mixture was cooled to room temperature and the pH adjusted to pH 6 using hydrochloric acid solution (2M) and the resulting precipitate was filtered and dried in vacuo to give the title compound (0.11 g, 78%) as an off-white solid.

Workup

  1. additionaddition the cooling bath
  2. customwas removed
  3. customthe reaction mixture was evaporated to dryness
  4. additionTo the residue was added sodium hydroxide solution (0.5 M, 5 ml)
  5. stirringthe mixture was stirred at 80° C. for 3 h
  6. temperatureThe mixture was cooled to room temperature
  7. filtrationthe resulting precipitate was filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-bf1242f4a62f4ab2a9d086f066f1c384
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Linked notes

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