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1,3-Propanediamine → HCID 12085954, 화합물

HRID 412695
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HRID 412695 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:35]=[CH:34][C:16]2[NH:17][C:18]([CH2:20][C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][C:29]([C:31]([OH:33])=O)=[CH:30][C:23]=4[N:22]=3)=[N:19][C:15]=2[CH:14]=1.ON1C2C=CC=CC=2N=N1.Cl.C[N:48](C)[CH2:49][CH2:50][CH2:51][N:52]=C=NCC.NCCCN.CN1CCOCC1>C(Cl)Cl.CN(C=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:35]=[CH:34][C:16]2[N:17]=[C:18]([CH2:20][C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][C:29]([C:31]([NH:48][CH2:49][CH2:50][CH2:51][NH2:52])=[O:33])=[CH:30][C:23]=4[N:22]=3)[NH:19][C:15]=2[CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 4281,3-PropanediamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178480115HCID 178480115, 화합물

생성물 1

HCID 12085954HCID 12085954, 화합물수율 35.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

2-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-1-methyl-1H-benzoimidazole-5-carboxylic acid (0.05 g, 0.108 mmol), 1-hydroxybenzotriazole (0.016 g, 0.118 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.023 g, 0.12 mmol) and the mono-BOC protected derivative of 1,3-diaminopropane were dissolved at 0° C. in methylene chloride (1 mL) and DMF (minimal amount sufficient to effect a solution). The solution was adjusted to pH-8 with N-methylmorpholine and the mixture was allowed to slowly warm to room temperature and then stirred for 20 hours. The mixture was transferred to a separatory finnel, diluted with methylene chloride, washed with 0.1N HCl solution and then saturated NaHCO3 solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparatory TLC (10% methanol/ethyl acetate) to provide 2-[6-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-1-methyl-N-(3-aminopropyl)-1H-benzoimidazole-5-carboxamide (0.02 g, 28% yield); 1H-NMR (300 Mhz, CDCL3): 7.75-7.81 (m, 4H), 7.61-7.68 (m, 3H), 7.33 (br s, 1H), 7.27 (d, 1H, J=8.6 Hz), 7.15 (d, 1H, J=9.3 Hz), 5.10 (br t, 1H), 4.90 (br s, 2H), 4.57 (s, 2H), 3.71 (s, 3H), 3.49 (q, 2H, J=7.2 Hz), 3.24 (q, 2H, J=7.2 Hz), 1.72 (m, 2H), 1.41 (s, 9H);

후처리

  1. washwashed with 0.1N HCl solution
  2. dry with materialsaturated NaHCO3 solution, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparatory TLC (10% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-d9aecf6aabbf415b80ba7c1e8ee109f4
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06562854B2

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