Diisopropylethylamine → 4-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-6-ethylpyridin-4-yl}methyl)-N-methylpiperazine-1-carboxamide

HRID 1814014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814014
Cl[CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)[CH:4]=1.[Cl-].[CH3:20][NH:21][C:22]([N:24]1[CH2:29][CH2:28][NH2+:27][CH2:26][CH2:25]1)=[O:23].C(N(C(C)C)C(C)C)C>CS(C)=O.O>[C:17]([C:14]1[S:13][C:12]([NH:11][C:5]2[CH:4]=[C:3]([CH2:2][N:27]3[CH2:28][CH2:29][N:24]([C:22]([NH:21][CH3:20])=[O:23])[CH2:25][CH2:26]3)[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]=2)=[N:16][CH:15]=1)#[N:18]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 225042962-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrileHCID 695511324-Methylcarbamoyl-piperazin-1-ium chloride

Produkt 1

HCID 102001074-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-6-ethylpyridin-4-yl}methyl)-N-methylpiperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (0.113 g, 0.41 mmol) was dissolved in 2 mL DMSO. 1-[(Methylamino)carbonyl]piperazin-4-ium chloride (0.146 g, 0.81 mmol) and N-ethyl-N,N-diisopropylamine (0.283 mL, 1.63 mmol) were added and the solution was stirred for 24 hours. The reaction was diluted with water and the resulting precipitate was filtered and washed with water. The precipitate was purified by flash column chromatography (gradient, 5-10% MeOH/CH2Cl2). The fractions containing the desired compound were concentrated to dryness to afford the desired product 12-4.

Aufarbeitung

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customThe precipitate was purified by flash column chromatography (gradient, 5-10% MeOH/CH2Cl2)
  4. additionThe fractions containing the desired compound
  5. concentrationwere concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c1c083e1210848f6b8da0a5ef0dcd9f7
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875767B2

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