1-Hydroxybenzotriazole → 4-Amino-3-(3-dipropylaminomethyl-benzoylamino)-benzoic acid methyl ester

HRID 2080768Notes

Reaction equation

HRID 2080768 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:40][O:41][C:42](=[O:51])[C:43]1[CH:48]=[CH:47][C:46]([NH2:49])=[C:45]([NH2:50])[CH:44]=1>C(Cl)(Cl)Cl>[CH3:40][O:41][C:42](=[O:51])[C:43]1[CH:48]=[CH:47][C:46]([NH2:49])=[C:45]([NH:50][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[C:9]([CH2:8][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH3:7])[CH:10]=2)[CH:44]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16776218HCID 16776218, compound

Product 1

HCID 671038094-Amino-3-(3-dipropylaminomethyl-benzoylamino)-benzoic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound (300 mg) obtained in Example 18-2, WSCI hydrochloride (365 mg), and HOBt (260 mg) were dissolved in chloroform (6.0 ml), and the whole was stirred for 1 hour. Then, 3,4-diaminobenzoic acid methyl ester (198 mg) was added thereto and the whole was stirred for 2 hours. A solid was precipitated, so DMF (2.0 ml) was added thereto and stirring was continued for additional 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Then, the residue was dissolved in chloroform and washed with a saturated ammonium chloride aqueous solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. Then, the resultant was dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (381 mg) as a brown oily substance.

Workup

  1. stirringthe whole was stirred for 2 hours
  2. customA solid was precipitated
  3. additionso DMF (2.0 ml) was added
  4. stirringstirring
  5. waitwas continued for additional 4 hours
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThen, the residue was dissolved in chloroform
  9. washwashed with a saturated ammonium chloride aqueous solution
  10. dry with materialThen, the resultant was dried with anhydrous sodium sulfate
  11. filtrationAfter filtration
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-0e6c9a1e05e54d5fb367a7ed6280acef
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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