Potassium Iodide → 4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7-[3-(pyrimidin-2-ylsulfanyl)-propoxy]-quinoline

HRID 8232

반응식

HRID 8232 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:19][N:18]4[CH2:27][CH2:28][CH2:29][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[SH:30][C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1.[I-].[K+]>CN(C)C=O>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]1[C:16]([C:10]2[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][S:30][C:31]4[N:36]=[CH:35][CH:34]=[CH:33][N:32]=4)=[CH:7][CH:8]=3)[N:13]=[CH:12][CH:11]=2)=[C:17]2[CH2:29][CH2:28][CH2:27][N:18]2[N:19]=1

참가 물질

5

반응물 3

HCID 4875Potassium IodideHCID 219925637-(3-Chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolineHCID 178418793HCID 178418793, 화합물

생성물 1

HCID 219926204-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7-[3-(pyrimidin-2-ylsulfanyl)-propoxy]-quinoline수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

7-(3-Chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (0.060 g, 0.148 mmol), 2-mercaptopyrimidine (0.033 g, 0.296 mmol, 2.0 equiv) and potassium iodide (0.010 g, 0.120 mmol, 0.80 equiv) are combined in N,N-dimethylformamide (1.0 mL) and the reaction is heated at 60° C. for 72 h. The mixture is placed on a 10 g SCX resin column. The resin is washed sequentially with 9:1 dichloromethane: methanol (2×120 mL), 4:1 dichloromethane: methanol (2 N ammonia) (2×125 mL), and methanol (2 N ammonia) (125 mL). The ammonia washes are evaporated to dryness and the residue is subjected to chromatography on silica gel (20 g, 99:1 dichloromethane: methanol (2 N ammonia)) to yield 0.054 g (76%) of the desired product as a tan solid.

후처리

  1. washThe resin is washed sequentially with 9:1 dichloromethane
  2. customThe ammonia washes are evaporated to dryness

출처 및 근거

ORD 기록
ord-b3764ff29850433d878043b9dcb90022
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

연결된 노트

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