n,n-Dimethylpiperazine-1-carboxamide → N-(1,3-Thiazol-2-yl)pyridin-2-amine 19

HRID 1355517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355517
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:4]=1.[CH3:17][N:18]([CH3:27])[C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20]>CS(C)=O.O>[C:15]([C:12]1[S:11][C:10]([NH:9][C:5]2[CH:4]=[C:3]([CH2:2][N:24]3[CH2:23][CH2:22][N:21]([C:19]([N:18]([CH3:27])[CH3:17])=[O:20])[CH2:26][CH2:25]3)[CH:8]=[CH:7][N:6]=2)=[N:14][CH:13]=1)#[N:16]

Komponenten

5

Edukt 2

HCID 712909n,n-Dimethylpiperazine-1-carboxamide2×HCID 11161046HCID 11161046, Verbindung

Produkt 1

HCID 5329332N-(1,3-Thiazol-2-yl)pyridin-2-amine 19

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-(4-Chloromethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (0.119 g, 0.47 mmol) was dissolved in 1 mL DMSO. N,N-Dimethyl-1-piperazinecarboxamide (0.149 g, 0.95 mmol) was added and the solution was stirred for 3.5 hr. Additional N,N-dimethyl-1-piperazinecarboxamide (0.149 g, 0.95 mmol) was added and the solution was stirred for 1.5 hr. The reaction was diluted with water and the resulting precipitate collected by filtration. The solid was washed with water and hexanes then air dried overnight to afford the free base. Free base: 1H NMR (CD3OD) δ 8.33 (d, 1H, J=5.0 Hz), 8.03 (s, 1H), 7.08 (s, 1H), 7.04 (d, 1H, J=5.0 Hz), 3.58 (s, 1H), 3.29 (t, 4H, J=6.0 Hz), 2.84 (s, 6H), 2.49 (t, 4H, J=Hz). MS [M+H]+=372.1611.

Aufarbeitung

  1. stirringthe solution was stirred for 1.5 hr
  2. filtrationthe resulting precipitate collected by filtration
  3. washThe solid was washed with water and hexanes
  4. customair dried overnight
  5. customto afford the free base

Quellen und Nachweise

ORD-Eintrag
ord-b67b6de0fc7b4255be7d141e5a2a5340
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586424B2

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