Isoquinoline-1-carboxylic acid → HCID 178481697, 화합물

HRID 33221

반응식

HRID 33221 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 178481697HCID 178481697, 화합물수율 78.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf1242f4a62f4ab2a9d086f066f1c384
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429579B2

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