Triethylamine → (R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one

HRID 2062211ノート

反応式

HRID 2062211 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2Cl.C(N(CC)CC)C.[OH:27][C@H:28]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:34]1[CH2:33][CH2:32][N:31]([C:29](=[O:30])[C@H:28]([OH:27])[CH2:37][CH:38]([CH3:39])[CH3:40])[CH2:36][CH2:35]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 59216548(R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-oneHCID 1361215002-(6-Bromo-4-chloroquinazolin-2-yl)phenol

生成物 1

HCID 136121577(R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(6-bromo-4-chloroquinazolin-2-yl)phenol (228 mg, 0.68 mmol), triethylamine (129 μL, 0.92 mmol), and CH2Cl2 (6 mL) was added (R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-one (185 mg, 0.92 mmol) dissolved in CH2Cl2 (3 mL). The flask was flushed with N2 and stirred for 3 hours. The reaction mixture was then transferred into a separatory funnel with CH2Cl2, and the organic phase was washed with H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0 to 20% EtOAc and CH2Cl2:hexanes (1:1) gave (R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one (285 mg, 84%). LC/MS: m/z 500.30 (M+H)+ at 3.29 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. customThe flask was flushed with N2
  2. customThe reaction mixture was then transferred into a separatory funnel with CH2Cl2
  3. washthe organic phase was washed with H2O (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification via silica gel chromatography

出典と根拠

ORDレコード
ord-fd2b1b47260b4c11a2ab9e193a994c5c
出典データセット
uspto-grants-2012_10
特許番号
US08283354B2

反応ノート

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