Pyridine → 3-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-naphthalene-2-carboxylic acid methyl ester

HRID 1095002

Reaction equation

HRID 1095002 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Cl)[CH:18]=2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].N1C=CC=CC=1.[CH3:32][CH:33]([OH:40])[CH2:34][NH:35][CH2:36][CH:37]([OH:39])[CH3:38].ClCC1C=C(C=CC=1)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:14]([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:35]([CH2:36][CH:37]([OH:39])[CH3:38])[CH2:34][CH:33]([OH:40])[CH3:32])[CH:18]=2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8086DiisopropanolamineHCID 2417523-(Chloromethyl)benzoic acidHCID 666381163-(3-Chloromethylbenzoylamino)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 666378043-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-naphthalene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, 3-(3-chloromethyl-benzoylamino)-naphthalene-2-carboxylic acid methyl ester (870 mg) was dissolved in anhydrous methylene chloride (15 ml). Pyridine (400 μl) and diisopropanolamine (compound B′) (1.0 g) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 48 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 3-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-naphthalene-2-carboxylic acid methyl ester as a useful intermediate (640 mg).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluted with a hexane-acetone system

Sources & evidence

ORD record
ord-b33e69d7d05747159e1ac4dc093c2c2f
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Linked notes

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