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

HRID 1355517노트

반응식

HRID 1355517 반응식
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]

참가 물질

5

반응물 2

HCID 712909n,n-Dimethylpiperazine-1-carboxamide2회HCID 11161046HCID 11161046, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b67b6de0fc7b4255be7d141e5a2a5340
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586424B2

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