1,3-Propanediamine → HCID 86634386, compound

HRID 1191290Notes

Reaction equation

HRID 1191290 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]1[CH2:25][C:26](O)=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:30]([CH3:33])C=O.C(N)CCN.O[N:40]1[C:44]2C=CC=C[C:43]=2[N:42]=[N:41]1>O.ClCCCl>[N:40]([CH2:44][CH2:43][CH2:33][NH:30][C:26](=[O:27])[CH2:25][CH:12]1[CH:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:15][CH2:16][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[N+:41]=[N-:42]

Participants

7

Reactant 4

HCID 4281,3-PropanediamineHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 68913569HCID 68913569, compound

Product 1

HCID 86634386HCID 86634386, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

The compound 25 (784 mg), dimethylformamide (8 mL), propane-1,3-diamine (300 mg), 1-hydroxybenzotriazole (297 mg) and 1,2-dichloroethane (575 mg) were stirred at room temperature for overnight. The reaction solution was added water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=66:34→0:100) to obtain the title compound (797 mg) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=66:34→0:100)

Sources & evidence

ORD record
ord-b0cfb6e000174da8b3f722e9a38b9ac4
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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