5-Nitro-2-Furoic Acid → HCID 16730809, 화합물

HRID 507337

반응식

HRID 507337 반응식
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:42]1[C:54]2[NH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[C:45]([O:55][CH2:56][CH:57]([OH:65])[CH2:58][N:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:44][CH:43]=1>CN(C=O)C.C(Cl)Cl>[CH:42]1[C:54]2[NH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[C:45]([O:55][CH2:56][CH:57]([OH:65])[CH2:58][N:59]2[CH2:64][CH2:63][N:62]([C:9]([C:7]3[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:61][CH2:60]2)=[CH:44][CH:43]=1

참가 물질

8

반응물 5

HCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16730483HCID 16730483, 화합물

생성물 1

HCID 16730809HCID 16730809, 화합물수율 51%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-Nitrofuroic acid (1.56 g, 9.9 mmol) in DMF (30 mL) was added DIPEA (4.3 mL, 24.8 mmol), EDCI (3.18 g, 16.5 mmol), HOBt (0.44 g, 3.3 mmol) followed by the 1-(9H-carbazol-4-yloxy)-3-piperazin-1-ylpropan-2-ol (2.7 g, 8.3 mmol, prepared following the procedure described above in step 11, example 26). The reaction mixture was stirred at room temperature for 12 hours and was diluted with DCM (100 mL), washed with water and brine solution. The organic layer was dried on anhydrous Na2SO4, concentrated and purified by silica gel column chromatography, using hexane/EtOAc (4:6) to afford the title compound as yellow colored solid (2.0 g, 51% yield) with m.p: 178-181° C. 1H NMR (400 MHz, DMSO): δ 2.30-2.60 (m, 4H), 2.67-2.69 (m, 2H), 3.63-3.69 (m, 4H), 4.13-4.21 (m, 3H), 5.08 (s, 1H), 6.69 (d, 1H, J=8.0 Hz), 7.06 (d, 1H, J=8.0 Hz), 7.14 (t, 1H, J=8.0 Hz), 7.24-7.36 (m, 3H), 7.44 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=4.0 Hz), 8.22 (d, 1H, 8.0 Hz), and 11.25 (s, 1H). MS m/z: 464.8 (M+1).

후처리

  1. customprepared
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried on anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b1f89fd6d798400ab29c3f617f4af488
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786142B2

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