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

HRID 2188245
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HRID 2188245 반응식
[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
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매
HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f1fbb5280bd14bc3873add411d26887e
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06410728B1

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