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Ethyl bromoacetate → Ethyl[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]acetate formic acid

HRID 2059926
ノート
印刷プレビュー

反応式

HRID 2059926 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][NH:22][CH2:23]4)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:30]([OH:32])=[O:31].[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:22]1[CH2:21][CH2:20][C:19]2[C:24](=[CH:25][CH:26]=[CH:27][C:18]=2[C:15]2[N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[C:6]([C:7]#[N:8])[CH:9]=3)[O:17][N:16]=2)[CH2:23]1)[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 441248992-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

生成物 1

HCID 131729974Ethyl[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]acetate formic acid

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A suspension of 2-[(1-methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile (Example 3, 28.8 mg, 0.080 mmol), ethyl bromoacetate (35.5 μl, 0.32 mmol) and Cs2CO3 (130 mg, 0.40 mmol) in DMF (2 mL) was stirred at room temperature for 1 h, and then irradiated to 60° C. for 5 min in the microwave. The suspension was added to an SCX cartridge, and the product eluted with methanolic ammonia. Concentration in vacuo gave a crude product (43 mg) that was purified by MDAP to give the title compound as a clear film (11.6 mg, 32%). 1H NMR (400 MHz, CDCl3) δ 8.41 (1H, d), 8.33 (1H, dd), 8.09 (1H, br. s), 8.01 (1H, d), 7.34 (1H, apparent t), 7.21 (1H, d), 7.12 (1H, d), 4.80 (1H, sept), 4.24 (2H, q), 4.00 (2H, s), 3.52 (2H, s), 3.35 (2H, t), 3.07 (2H, t), 1.48 (6H, d), 1.31 (3H, t); m/z (ES) 447 [M+H]+.

後処理

  1. customirradiated to 60° C. for 5 min in the microwave
  2. additionThe suspension was added to an SCX cartridge
  3. washthe product eluted with methanolic ammonia
  4. concentrationConcentration in vacuo
  5. customgave a crude product (43 mg) that
  6. customwas purified by MDAP

出典と根拠

ORDレコード
ord-f5646bcb51044bdd9cbbbd4be5649cc0
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08278324B2

反応ノート

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