1-Hydroxybenzotriazole → 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1445939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445939
NC(=O)C([C:5]1[C:9]2[C:10]([O:14][CH2:15]C(O)=O)=[N:11][CH:12]=[CH:13][C:8]=2[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]=1[CH3:26])=O.C(OC(=O)[C@H](CC(OCC1C=CC=CC=1)=O)N)C1C=CC=CC=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1.ClCCl>[CH2:19]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH3:15])[C:9]=2[CH:5]=[C:6]1[CH3:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2808532(S)-Dibenzyl 2-aminosuccinateHCID 166569372-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)acetic acid

Produkt 1

HCID 591703081-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)acetic acid ILY-II-1 (1.5 mmol) in dichloromethane/dimethylformamide (5:1) is added aspartic acid dibenzyl ester (313 mg 1.5 mmol), 4-dimethylaminopyridine (18 mg 0.15 mmol), 1-hydroxybenzotriazole (202 mg, 1.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (286 mg, 1.5 mmol), respectively and reaction mixture allows to stir at room temperature. After 6 hrs the reaction is diluted with dichloromethane and washed twice with 1N HCl and brine. The organic layer is dried with Na2SO4 and evaporated in vacuum. The residue is chromatographed on silica gel to give the titled compound 2.

Aufarbeitung

  1. customrespectively and reaction mixture
  2. washwashed twice with 1N HCl and brine
  3. dry with materialThe organic layer is dried with Na2SO4
  4. customevaporated in vacuum
  5. customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-99732d84c1b14bfbaf23e9d01cbbf628
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666898B2

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