1-Hydroxybenzotriazole → 4-{[N-Boc-N-(1H-imidazol-2-ylmethyl)amino]methyl}-N-(4-dipropylaminobutyl)benzamide

HRID 2080724Notes

Reaction equation

HRID 2080724 reaction equation
[CH2:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9])[CH2:2][CH3:3].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:35]([O:39][C:40]([N:42]([CH2:49][C:50]1[CH:58]=[CH:57][C:53]([C:54](O)=[O:55])=[CH:52][CH:51]=1)[CH2:43][C:44]1[NH:45][CH:46]=[CH:47][N:48]=1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C.C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:35]([O:39][C:40](=[O:41])[N:42]([CH2:49][C:50]1[CH:51]=[CH:52][C:53]([C:54](=[O:55])[NH:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:10][CH2:11][CH3:12])=[CH:57][CH:58]=1)[CH2:43][C:44]1[NH:48][CH:47]=[CH:46][N:45]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7138396N,N-dipropylbutane-1,4-diamineHCID 219736124-((((1H-imidazol-2-yl)methyl)(tert-butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 210844754-{[N-Boc-N-(1H-imidazol-2-ylmethyl)amino]methyl}-N-(4-dipropylaminobutyl)benzamideYield 29.4%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The compound (203 mg) obtained in Example 1-2 was dissolved in DMF (5.0 ml) and chloroform (5.0 ml), and then added with triethylamine (0.374 ml), WSCI hydrochloride (382 mg), HOBt (200 mg), and the compound (463 mg) obtained in Example 6-1. The whole was stirred at room temperature for 23 hours. After completion of the reaction, the solvent was distilled off. Then, the resultant was added with chloroform and washed with water and a saturated saline solution, followed by drying with anhydrous sodium sulfate. The solvent was distilled off and the residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (168 mg) as colorless foam.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThen, the resultant was added with chloroform
  4. washwashed with water
  5. dry with materialby drying with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-1b19a98b80a345259d96ff062d948ab1
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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