Boron tribromide → HCID 178515837、化合物

HRID 69172ノート

反応式

HRID 69172 の反応式
B(Br)(Br)Br.C[O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)=[CH:20][N:21]=3)[N:18]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[N:29]1[C:30]2[C:25](=[CH:24][C:23]([CH2:22][C:19]3[N:17]4[N:18]=[C:13]([C:10]5[CH:9]=[CH:8][C:7]([OH:6])=[N:12][CH:11]=5)[CH:14]=[CH:15][C:16]4=[N:21][CH:20]=3)=[CH:32][CH:31]=2)[CH:26]=[CH:27][CH:28]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 442081346-[6-(6-Methoxypyridin-3-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

生成物 1

HCID 178515837HCID 178515837、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Boron tribromide (1364 mg, 5.44 mmol) was added to a suspension of 6-[6-(6-Methoxypyridin-3-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline (Example 62, 200 mg, 0.544 mmol) in DCM (5 mL) at −78° C. The RM was stirred at −78° C. for 15 min and then allowed to reach rt. It was then stirred at rt for 68 h. The RM was filtered and the obtained solid was purified by reverse phase chromatography (water 0.1% TFA/acetonitrile +0.1% TFA). The resulting oil precipitated in TBME/MeOH to afford the title compound as a white powder (tR 4.21 min (conditions 4), MH+=354.3, 1H-NMR in DMSO-d6: 9.00 (m, 1H); 8.58 (m, 1H); 8.31 (m, 2H); 8.19 (dd, 1H); 8.05 (m, 4H); 7.92 (dd, 1H); 7.70 (dd, 1H); 6.54 (d, 1H); 4.65 (s, 2H)).

後処理

  1. customto reach rt
  2. stirringIt was then stirred at rt for 68 h
  3. filtrationThe RM was filtered
  4. customthe obtained solid was purified by reverse phase chromatography (water 0.1% TFA/acetonitrile +0.1% TFA)
  5. customThe resulting oil precipitated in TBME/MeOH

出典と根拠

ORDレコード
ord-f9acde036acc428896a602e197ba51f8
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

反応ノート

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