Pyridine → 2-Chloro-N-{4-methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-acetamide

HRID 32366

Reaktionsgleichung

Reaktionsgleichung von HRID 32366
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.[Cl:24][CH2:25][C:26](Cl)=[O:27].N1C=CC=CC=1.CC#N>CN(C=O)C.C(O)(C(F)(F)F)=O>[Cl:24][CH2:25][C:26]([NH:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1)=[O:27]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6342Acetonitrile2×HCID 6577Chloroacetyl chlorideHCID 4479614-(2-Amino-4-methyl-5-thiazolyl)-N-(3-nitrophenyl)-2-pyrimidinamine

Produkt 1

HCID 101793942-Chloro-N-{4-methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel2×

Versuchsvorschrift

A solution of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine (0.33 g, 1.0 mmol) in dry DMF (3 mL) was cooled on an ice-water bath. Chloroacetyl chloride (0.22 g, 2.0 mmol) and pyridine (80 μL) were added. After stirring at room temperature for 18 h, the product was isolated as a brown solid by preparative RP-HPLC (Vydac 218TP1022, 9 mL/min) using a gradient from 10-70% MeCN in 0.1% aq CF3COOH over 40 min. Anal. RP-HPLC: tR=20.62 min (Vydac 218TP54, 0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, 25° C., purity >97%). 1H-NMR (DMSO-d6) δ: 2.45 (s, 3H, CH3), 4.12 (s, 2H, CH2), 7.03(d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.42 (m, 1H, Ph-H), 7.63 (m, 1H, Ph-H), 8.01 (m, 1H, Ph-H), 8.41 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.64 (s, 1H, Ph-H).

Aufarbeitung

  1. customthe product was isolated as a brown solid by preparative RP-HPLC (Vydac 218TP1022, 9 mL/min)
  2. customover 40 min

Quellen und Nachweise

ORD-Eintrag
ord-0d39e5ff92d142fabe80ee9484ee6075
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427627B2

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