Benzaldehyde → N-{5-[5-(Benzylamino)-6-chloropyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide

HRID 252704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252704
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].Cl[Si](C)(C)C>CN1C(=O)CCC1.C(O)(=O)C>[CH2:19]([NH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 4

HCID 240BenzaldehydeHCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 86244450N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

Produkt 1

HCID 11501639N-{5-[5-(Benzylamino)-6-chloropyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamideAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (30 mg, 0.11 mmol), benzaldehyde (0.016 mL, 0.16 mmol) and sodium cyanoborohydride (13 mg, 0.21 mmol) were mixed in NMP (0.9 mL) and acetic acid (0.1 mL). Chlorotrimethylsilane (0.04 mL, 0.32 mmol) was added and the mixture was stirred overnight. The reaction product was purified by preparative HPLC (Method A) to give the title product (retention time 9.73 minutes; 19 mg); 1H NMR Spectrum: (DMSOd6) 12.13 (1H, s); 7.60 (1H, d); 7.38-7.30 (4H, m); 7.22 (1H, t); 6.80 (1H, d); 6.67 (1H, s); 4.47 (2H, s); 2.12 (3H, s); 2.03 (3H, s); Mass Spectrum: M+H+ 373 and 375.

Aufarbeitung

  1. customThe reaction product was purified by preparative HPLC (Method A)

Quellen und Nachweise

ORD-Eintrag
ord-41f9b66c677d4434bd97f9876f554b7f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868188B2

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