HCID 11504490、化合物 → HCID 57736689、化合物

HRID 2080345ノート

反応式

HRID 2080345 の反応式
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH3:21])[CH2:16]3)[CH:9]=2)=[CH:6][C:5]([CH2:22][NH:23][C:24](=O)[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:26]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH3:21])[CH2:16]3)[CH:9]=2)=[CH:6][C:5]([CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:26]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 11504490HCID 11504490、化合物HCID 21226445Aluminium lithium hydride

生成物 1

HCID 57736689HCID 57736689、化合物収率 82.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A solution of N-[(6-fluoro-3′-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-3-(4-piperidinylmethyl)benzamide (100 mg, 0.194 mmol) in THF (2.0 mL) was added to lithium aluminum hydride (1.0 N in THF, 2 mL, 2 mmol). The mixture was heated in a microwave reactor at 80° C. for 60 minutes. After cooling to room temperature, the reaction mixture was carefully quenched with saturated Na2SO4, filtered through celite, dried over K2CO3 and concentrated under vacuum to give a crude oil. Further purification by Gilson reverse phase HPLC, eluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min), gave the title compound (80 mg, 82%) as an oil. LC/MS: m/z, 502 (M+H), 1.29 min.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was carefully quenched with saturated Na2SO4
  3. filtrationfiltered through celite
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated under vacuum
  6. customto give a crude oil
  7. customFurther purification by Gilson reverse phase HPLC
  8. washeluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min)

出典と根拠

ORDレコード
ord-38cc27f74241456f8f9831e775ef98a6
出典データセット
uspto-grants-2011_04
特許番号
US07932247B2

反応ノート

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