Diethyl chlorophosphate → HCID 11350137, 화합물

HRID 1091460

반응식

HRID 1091460 반응식
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[P:21](Cl)([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH2:24]([O:23][P:21]([NH:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3)(=[O:22])[O:26][CH2:27][CH3:28])[CH3:25]

참가 물질

4

반응물 2

HCID 13139Diethyl chlorophosphateHCID 1119635510-(Aminomethyl)[1]benzopyrano[4,3,2-de]phthalazin-3(2H)-one

생성물 1

HCID 11350137HCID 11350137, 화합물수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 49 (0.5 mmol) in anhydrous DMF (20 mL) was added diethyl chlorophosphate (1.5 mmol). After 3 hours solution was concentrated in vacuo, and 50 mL of water was added. The aqueous layer was extracted with 30 mL of EtOAc twice. Organic layers were combined and washed with 30 mL of brine. Organic layer was dried with MgSO4. Solvent was removed to afford a white solid, which was recrystallized in 10% of EtOAc in hexanes to afford a white solid 54 in 50% yield. MS (ES−): 400; Mp: 222.3-224.5° C.; 1H-NMR (CDCl3, 400 MHz): 10.21 (s, 1H), 8.10 (d, J=2.5 Hz, 1H), 8.03 (d, J=7.5 Hz, 1H), 7.79 (t, J=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.47 (dd, J=8.5 and 2.0 Hz, 1H), 7.22 (d, J=8.5 Hz, 1H), 4.12 (m, 6H), 1.32 (t, J=6.5 Hz, 6H); Anal. Calcd. for C19H20N3O5P.(0.3H2O): C, 56.10; H, 5.10; N, 10.33. Found: C, 56.00; H, 5.03; N, 10.13.

후처리

  1. concentrationAfter 3 hours solution was concentrated in vacuo, and 50 mL of water
  2. additionwas added
  3. extractionThe aqueous layer was extracted with 30 mL of EtOAc twice
  4. washwashed with 30 mL of brine
  5. dry with materialOrganic layer was dried with MgSO4
  6. customSolvent was removed
  7. customto afford a white solid, which
  8. customwas recrystallized in 10% of EtOAc in hexanes

출처 및 근거

ORD 기록
ord-8e4c477adf3d49379c26682630909732
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129382B2

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