1-Hydroxybenzotriazole → 6-benzyloxy-2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-7-carboxylic acid [3-(4-fluoro-phenyl)-2-oxo-propyl]-amide

HRID 1968430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968430
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:19])[S:18][C:12]2=[N:11][C:10]=1[C:20](O)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][CH2:25][C:26](=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][C:26](=[O:35])[CH2:25][NH:24][C:20]([C:10]2[N:11]=[C:12]3[S:18][C:17]([CH3:19])=[CH:16][N:13]3[C:14](=[O:15])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:21])=[CH:33][CH:32]=1

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 585144576-benzyloxy-2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-7-carboxylic acid

Produkt 1

HCID 670052056-benzyloxy-2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-7-carboxylic acid [3-(4-fluoro-phenyl)-2-oxo-propyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product of example 1 (2.4 mmol) in THF (10 ml) was added compound 1-amino-3-(4-fluoro-phenyl)-propan-2-one hydrochloride (1.0 g, 4.9 mmol), EDCI.HCl (560 mg, 2.9 mmol), HOBt (400 mg, 2.9 mmol) and TEA (1 g, 9.9 mmol), successively at room temperature. The mixture was stirred overnight, after which saturated sodium bicarbonate was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, and then dried over sodium sulfate. The product was purified by column chromatography to give the desired product.

Aufarbeitung

  1. customsuccessively at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3226fc47e52e4e29a53985d1a949dfc2
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426405B2

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