Tetrahydrofuran → HCID 178519657、化合物

HRID 505543ノート

反応式

HRID 505543 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([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:9]=1)[C:5]#N.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:40]CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([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:9]=1)[CH:5]=[O:40]

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 21226445Aluminium lithium hydrideHCID 178509924HCID 178509924、化合物

生成物 1

HCID 178519657HCID 178519657、化合物

実験手順

To 3-chloro-5-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile (10 mg, 0.023 mmol) dissolved in dry THF (0.5 mL) at 0° C. was added LAH solution 1M in THF (0.046 mL, 0.046 mmol). After 30 minutes, the reaction was quenched with EtOAc (2 mL) at 0° C., followed by addition of saturated aqueous Na2SO4 (0.25 mL), and then after 5 minutes by addition of water (0.5 mL). This mixture was allowed to stir for 5 minutes after which time solid Na2SO4 was added to the reaction mixture. The dried mixture was then filtered and solvent removed under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions were lyophilized to afford the title compound. 1H NMR (DMSO-d6) δ 9.90 (s, 1H), 8.52 (d, J=3.5 Hz), 8.10 (d, J=7.5 Hz), 7.90 (d, J=8.9 Hz, 1H), 7.80 (d, J=8.9 Hz, 1H), 7.72 (m, 1H), 7.30 (m, 1H), 7.20 (dd, J=8.1 Hz, J=4.6 Hz, 1H), 6.40 (s, 2H).

後処理

  1. customthe reaction was quenched with EtOAc (2 mL) at 0° C.
  2. additionfollowed by addition of saturated aqueous Na2SO4 (0.25 mL)
  3. additionafter 5 minutes by addition of water (0.5 mL)
  4. additionwas added to the reaction mixture
  5. filtrationThe dried mixture was then filtered
  6. customsolvent removed under reduced pressure
  7. customThe resulting residue was purified by reverse phase chromatography
  8. washeluting with 30-95% MeCN/H2O+0.1% TFA

出典と根拠

ORDレコード
ord-2cc0e485a1c6413e8cba5c14cbbfcbb0
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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