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Diisopropylamine → N-(3-(3-Fluoro-4-(7H-purin-6-ylethynyl)-phenyl)-2-oxo-oxazolidin-5-ylmethl)-acetamide

HRID 2188245
ノート
印刷プレビュー

反応式

HRID 2188245 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])=[CH:5][C:4]=1[F:20])#[CH:2].C(NC(C)C)(C)C.I[C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[NH:31][CH:32]=[N:33]2>CN(C=O)C.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:20][C:4]1[CH:5]=[C:6]([N:9]2[CH2:13][CH:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:7]=[CH:8][C:3]=1[C:1]#[C:2][C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[NH:31][CH:32]=[N:33]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 7912DiisopropylamineHCID 54630676-Iodo-9H-purineHCID 59908254N-(((5S)-3-(4-ethynyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide

生成物 1

HCID 22447480N-(3-(3-Fluoro-4-(7H-purin-6-ylethynyl)-phenyl)-2-oxo-oxazolidin-5-ylmethl)-acetamide

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒
HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a suspension of Example 3B (100 mg) and diisopropylamine (0.25 mL) in degassed DMF (1 mL) was added sequentially 6-iodopurine (89 mg), copper iodide (3.5 mg) and tetrakis(triphenylphosphine)palladium (21 mg). The mixture was heated to 60° C. for 4 hours. Next, the reaction mixture was cooled to room temperature and concentrated. The resultant material was dissolved in dichloromethane (4 mL), then filtered. The precipitate was washed with water (10 mL), then cold acetone (3 mL) to provide the desired solid. MS (ESI(+)) m/e 395 (M+H)+; 1H NMR (300 MHz, DMSO) δ 8.91 (s, 1H), 8.69 (s, 1H), 8.25 (t, J=5.7 Hz, 1H), 7.89 (m, 1H), 7.82 (t, J=9 Hz, 1H), 7.7 (dd, J=2.1, 12.3 Hz, 1H), 7.5 (dd, J=2.1, 9 Hz, 1H), 4.78 (m, 1H), 4.19 (t, J=9 Hz, 1H), 3.8 (dd, J=6.3, 9.6 Hz, 1H), 3.44 (t, J=5.7 Hz, 2H), 1.84 (s, 3H).

後処理

  1. temperatureNext, the reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe resultant material was dissolved in dichloromethane (4 mL)
  4. filtrationfiltered
  5. washThe precipitate was washed with water (10 mL)
  6. customcold acetone (3 mL) to provide the desired solid

出典と根拠

ORDレコード
ord-f1fbb5280bd14bc3873add411d26887e
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06410728B1

反応ノート

読み込み中…

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