1,3-Propanediamine → HCID 12085954, compound

HRID 412695Notes

Reaction equation

HRID 412695 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

HCID 12085954HCID 12085954, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

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);

Workup

  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)

Sources & evidence

ORD record
ord-d9aecf6aabbf415b80ba7c1e8ee109f4
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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