1,2-Dichloroethane → HCID 9892498, 화합물

HRID 2220109노트

반응식

HRID 2220109 반응식
C[N:2]1[C:9](=O)[CH2:8][C:6](=[O:7])N(C)C1=O.[NH2:12][C:13]1[CH:36]=[CH:35][C:16]([C:17]([NH:19][CH:20]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[C:28](O)=[O:29])=[O:22])=[O:18])=[CH:15][C:14]=1[Cl:37].C(N(C(C)C)CC)(C)C.C(Cl)CCl.[CH3:51][CH2:52][O:53][C:54](C)=[O:55]>C(Cl)Cl.CN(C=O)C.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>[CH2:52]([O:53][CH:54]1[CH:9]([NH:2][C:28]([CH:24]2[CH2:25][CH2:26][CH2:27][N:23]2[C:21](=[O:22])[CH:20]([NH:19][C:17](=[O:18])[C:16]2[CH:35]=[CH:36][C:13]([NH2:12])=[C:14]([Cl:37])[CH:15]=2)[C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:8][C:6](=[O:7])[O:55]1)[CH3:51]

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 69860Dimethylbarbituric acidHCID 81531DiisopropylethylamineHCID 10156704VX-765

생성물 1

HCID 9892498HCID 9892498, 화합물수율 77%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 6 (5.05 g, 22.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added 1,3-dimethylbarbituric acid (DMBA) (3.78 g, 24.2 mmol)and Pd(PPh3)4 (0.15 g, 0.13 mmol) After 10 minutes, a solution of 5 (8.40 g, 22.0 mmol) in DMF (25 mL) was added followed by diisopropylethylamine (DIPEA) (7.66 mL, 44.1 mmol), (2.98 g, 22.0 mmol) and EDC (5.06 g, 26.4 mmol). The solution was stirred at 0° C. for 10 minutes then at room temperature for 18 hours. The reaction was diluted with EtOAc (200 mL), washed with 0.5N NaHSO4 (2×200 mL), 10% NaHCO3 (2×200 mL), saturated NaCl (1×150 mL), dried over anhydrous MgSO4, and evaporated to dryness. Flash column chromatography on silica gel using CH2Cl2/MeOH, (99/1 to 98/2%) afforded the title compound as a white solid (11.20 g, 77% yield): 1H-NMR (500 MHz, CDCl3) δ1.08 (s, 9H), 1.27 (t, 3H), 1.85–1.99 (m, 1H), 2.00–2.06 (m. 1H), 2.07–2.18 (m, 1H), 2.32–2.48 (m, 2H), 2.78–2.89 (m, 1H), 3.62–3.76 (m, 2H), 3.82–3.96 (m, 2H), 4.39 (s, 1H), 4.54–4.60 (m, 1H), 4.62–4.76 (m, 1H), 4.85 (d, 1H), 6.57 (d, 1H), 6.73 (d, 1H), 7.38 (d, 1H), 7.49 (d, 1H), 7.72 (s, 1H). Analytical HPLC (cyano column): 13.10 min. LC-MS (ES+) m/e=509.4 (M+H), m.p.=96–99 ° C.

후처리

  1. waitat room temperature for 18 hours
  2. washwashed with 0.5N NaHSO4 (2×200 mL), 10% NaHCO3 (2×200 mL), saturated NaCl (1×150 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-d36a7cd1659745388ba6f7a58aa52967
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417029B2

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