1-Hydroxybenzotriazole → 5-Amino-4-methyl-2-(1-methyl-piperidin-4-yl)-6-nitro-isoindole-1,3-dione

HRID 929089노트

반응식

HRID 929089 반응식
CO[C:3](=[O:18])[C:4]1[C:5](=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([NH2:14])[C:12]=1[CH3:13])[C:6]([OH:8])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[NH2:43][CH:44]1[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]1>CCN(CC)CC>[NH2:14][C:11]1[C:12]([CH3:13])=[C:4]2[C:5](=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])[C:6](=[O:8])[N:43]([CH:44]1[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]1)[C:3]2=[O:18]

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220025361-Methylpiperidin-4-amine dihydrochlorideHCID 597616804-Amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acid

생성물 1

HCID 597618595-Amino-4-methyl-2-(1-methyl-piperidin-4-yl)-6-nitro-isoindole-1,3-dione수율 104.3%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a solution of 4-Amino-3-methyl-5-nitro-phthalic acid 2-methyl ester (1.3 g, 5.12 mmol), EDCI.HCl (1.07 g, 5.63 mmol) and HOBt (0.69 g, 5.12 mmol) was added Et3N (3.64 mL, 25.6 mL) and stirred at room temperature for 10 min. 4-Amino-1-methylpiperidine dihydrochloride (1.04 g, 5.63 mmol) was added and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was evaporated in vacuo, the residue was dissolved in CHCl3 (200 mL), washed with water (2×100 mL). The organic layer was filtered over Na2SO4 and concentrated in vacuo to afford 5-Amino-4-methyl-2-(1-methyl-piperidin-4-yl)-6-nitro-isoindole-1,3-dione (1.7 g, quant), which was used as such for further reaction.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 24 h
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in CHCl3 (200 mL)
  4. washwashed with water (2×100 mL)
  5. filtrationThe organic layer was filtered over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fe9cbe9afa6d4e089473d5ffa9092dac
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290503B2

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