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2-(Dimethylamino)ethanol → HCID 23139421、化合物

HRID 540592
ノート
印刷プレビュー

反応式

HRID 540592 の反応式
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[O:17])[CH:11]=[CH:12][C:13]=1[OH:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[O:17])[CH:11]=[CH:12][C:13]=1[O:14][CH2:49][CH2:48][N:47]([CH3:51])[CH3:46]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 135732703HCID 135732703、化合物

生成物 1

HCID 23139421HCID 23139421、化合物収率 31.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

Compound 103 (73.7 mg, 0.17 mmol) was dissolved in anhydrous THF (5 mL). PPh3 (173 mg, 0.64 mmol) and 2-Dimethylamino ethanol (65.5 μL, 0.63 mmol) were then added to the solution, and the reaction was stirred at room temperature. After stirring for five minutes, DIAD (127 μL, 0.64 mmol) was added to the reaction dropwise. The reaction was found to be complete by TLC and LC/MS after 30 minutes. The solvent was then removed under reduced pressure. The residue was purified twice by flash chromatography (Biotage, SiO2, Dichloromethane/Methanol gradient elution) and twice by HPLC to afford 26.4 mg (31%) of Compound 123 as a light brown oil: LCMS m/z (%)=496 (M+H81Br, 100), 494 (M+H79Br, 94). 1H NMR (400 MHz, DMSO-d6) δ 8.99 (s, 1H), 8.44 (s, 1H), 8.07-8.01 (m, 1H), 7.59 (s, 1H), 7.52 (dd, J1=8 Hz, J2=4 Hz, 1H), 7.35 (d, J=4, 1H), 7.32-7.26 (m, 1H), 7.17 (d, J=12 Hz, 1H), 7.05-7.00 (m, 1H), 4.11 (dm, 2H), 3.65 (s, 3H), 2.58 (dm, 2H), 2.11 (s, 6H).

後処理

  1. stirringAfter stirring for five minutes
  2. customThe solvent was then removed under reduced pressure
  3. customThe residue was purified twice by flash chromatography (Biotage, SiO2, Dichloromethane/Methanol gradient elution) and twice by HPLC

出典と根拠

ORDレコード
ord-f7a662633098450da456bb4e49b726d9
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871797B2

反応ノート

読み込み中…

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