Triethylamine → [(6-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-methyl-amino]-acetic acid

HRID 908798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908798
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:19])=[N:14][C:13]([C:20]([OH:22])=O)=[C:12]2[OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:56][NH:57][CH2:58][C:59]([O:61]CC)=[O:60]>ClCCl.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:19])=[N:14][C:13]([C:20]([N:57]([CH2:58][C:59]([OH:61])=[O:60])[CH3:56])=[O:22])=[C:12]2[OH:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 186981356-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid

Produkt 1

HCID 86595476[(6-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-methyl-amino]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

6-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid, 0.33 g, 0.5 ml of triethylamine, 0.400 g of HATU, and 0.165 g of ethyl N-methyl-amino-acetate hydrochloride were combined in 15 ml of dichloromethane and the reaction mixture was stirred at room temperature for 18 h to give, after silica gel chromatography, 0.232 g of an off-white solid, MS-(+)-ion: 429.0 amu. 0.208 g of this intermediate product were dissolved in 10 ml of methanolic NaOH (1.5 M) and the mixture was stirred at room temperature for 3 h. The solvent was removed with a rotary evaporator, the residue was dissolved in water, and the aqueous layer was extracted with 50 ml of ethyl acetate. The aqueous layer was acidified to pH=1 with aqueous HCl to give a solid precipitate. The solid was collected by suction filtration, washed with water, and dried in a vacuum oven (80° C.) to give 0.180 g of white solid: MS-(+)-ion: 401.0 amu.

Aufarbeitung

  1. customto give
  2. stirringthe mixture was stirred at room temperature for 3 h
  3. customThe solvent was removed with a rotary evaporator
  4. dissolutionthe residue was dissolved in water
  5. extractionthe aqueous layer was extracted with 50 ml of ethyl acetate
  6. customto give a solid precipitate
  7. filtrationThe solid was collected by suction filtration
  8. washwashed with water
  9. customdried in a vacuum oven (80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-e644c192406445628f1ec996ef710b99
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017625B2

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