Dichloromethane → 2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-6-(morpholinocarbonyl)-imidazo[1,2-a]pyridine

HRID 427474

Reaktionsgleichung

Reaktionsgleichung von HRID 427474
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([OH:23])=O)=[CH:6][N:5]2[C:24]=1[CH3:25].[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.C(Cl)Cl.[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1>C(OC(=O)C)C.C(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[O:23])=[CH:6][N:5]2[C:24]=1[CH3:25]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118239362,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid

Produkt 1

HCID 98226342,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-6-(morpholinocarbonyl)-imidazo[1,2-a]pyridineAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid (0.15 g, 0.44 mmol) and o-Benzotriazol-1-yl-N,N,N′,N′-Tetramethyluronium tetrafluoroborate (TBTU)(0.14 g, 0.44 mmol) were added to methylene chloride (10 ml). Morpholine (0.12 g, 1.4 mmol) was added and the reaction mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was added to a column with silica gel and purification by chromatography using ethylacetate:methylene chloride (1:1) as eluent gave 0.12 g (66%) of the desired product.

Aufarbeitung

  1. additionThe reaction mixture was added to a column with silica gel and purification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5373ac6385da469d951ad508a2b22454
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313136B1

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