5-Azaindole → 4-(Benzyloxycarbonyl)-1-(2-pyrrolo[3,2-c]pyridin-1-ylethyl)-piperazin-2-one

HRID 1432941ノート

反応式

HRID 1432941 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29]I)[C:24](=[O:31])[CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[CH:3]=[CH:2]2)[C:24](=[O:31])[CH2:23]1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 92205-AzaindoleHCID 24758Sodium hydrideHCID 536719754-(Benzyloxycarbonyl)-1-(2-iodoethyl)-piperazin-2-one

生成物 1

HCID 540369894-(Benzyloxycarbonyl)-1-(2-pyrrolo[3,2-c]pyridin-1-ylethyl)-piperazin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(Benzyloxycarbonyl)-1-(2-hydroxyethyl)-piperazin-2-one, prepared as described in EXAMPLE 94, part A. (0.26 g, 0.94 mmol) in methylene chloride (6 mL) is treated with triphenyl phosphine (0.60 g, 2.3 mmol), imidazole (0.16 g, 2.3 mmol), and iodine (0.47 g, 1.9 mmol) for 0.5 h at 0° C. The reactin mixture is partitioned between water and methylene chloride; the organic layer is concentrated and the residue is chromatographed (15% EtOAc/methylene chloride) to give 4-(benzyloxycarbonyl)-1-(2-iodoethyl)-piperazin-2-one (0.24 g, 0.62 mmol). Pyrrolo[3,2-c]pyridine (0.073 g, g, 0.62 mmol) is dissolved in DMF (3 mL) and treated with 60% sodium hydride (0.03 g, 0.74 mmol) and all of the 4-(benzyloxycarbonyl)-1-(2-iodoethyl)-piperazin-2-one from the previous step; the reaction mixture is stirred at r.t. for 16 g. The reaction mixture is concentrated to dryness and the residue is partitioned between water and methylene chloride. The organic layer is concentrated and subjected to chromatography (2-5% MeOH/methylene chloride) to yield the title compound (0.028 g, 0.074 mmol) Ion Spray MS m/z: 379, [M+1]+.

後処理

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customthe residue is partitioned between water and methylene chloride
  3. concentrationThe organic layer is concentrated

出典と根拠

ORDレコード
ord-fbb93015396849e78ace86bd2faefd39
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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