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

HRID 1355517Notes

Reaction equation

HRID 1355517 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b67b6de0fc7b4255be7d141e5a2a5340
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

Loading…