Aluminium lithium hydride → HCID 178509926、化合物

HRID 505555ノート

反応式

HRID 505555 の反応式
[Cl:1][C:2]1[C:9]([O:10][C:11]2[C:19]3[N:18]=[N:17][N:16]([CH2:20][C:21]4[C:29]5[C:24](=[N:25][CH:26]=[CH:27][CH:28]=5)[NH:23][N:22]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:30])=[CH:8][C:7]([Cl:31])=[CH:6][C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[C:9]([O:10][C:11]2[C:19]3[N:18]=[N:17][N:16]([CH2:20][C:21]4[C:29]5[C:24](=[N:25][CH:26]=[CH:27][CH:28]=5)[NH:23][N:22]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:30])=[CH:8][C:7]([Cl:31])=[CH:6][C:3]=1[CH2:4][NH2:5]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 178509925HCID 178509925、化合物

生成物 1

HCID 178509926HCID 178509926、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

2,5-dichloro-3-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile (283 mg, 0.601 mmol) was dissolved in dry THF (30 mL), cooled to 0° C., and LAH solution (1.20 mL, 1.20 mmol) in THF (1.2 mL) was added. The reaction mixture was allowed to warm to room temperature, and after 2 hours the mixture was cooled to 0° C. and quenched with EtOAc (50 mL). To this mixture was added saturated aqueous Na2SO4 (3 mL), followed 5 minutes later by the addition of water (5 mL). This mixture was stirred for 5 minutes after which excess solid Na2SO4 was added. The mixture was then filtered and solvent removed under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 5-95% MeCN/H2O+0.1% TFA to yield the title compound. 1H NMR (DMSO-d6) δ 8.53 (d, J=4.5 Hz, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.98 (s, 2H), 7.89 (d, J=9.0 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.48 (s, 1H), 7.20 (dd, J=8.0 Hz, J=4.5 Hz, 1H), 6.91 (s, 1H), 6.38 (s, 2H), 4.21 (s, 2H). HRMS (M+1)=476.0363.

後処理

  1. temperatureto warm to room temperature
  2. temperatureafter 2 hours the mixture was cooled to 0° C.
  3. customquenched with EtOAc (50 mL)
  4. additionTo this mixture was added saturated aqueous Na2SO4 (3 mL)
  5. additionfollowed 5 minutes later by the addition of water (5 mL)
  6. additionwas added
  7. filtrationThe mixture was then filtered
  8. customsolvent removed under reduced pressure
  9. customThe resulting residue was purified by reverse phase chromatography
  10. washeluting with 5-95% MeCN/H2O+0.1% TFA

出典と根拠

ORDレコード
ord-1d3b12ecd7334b7b9d699890c98b3299
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

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