1,2-Dichloroethane → {8-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol

HRID 1678777노트

반응식

HRID 1678777 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[NH:28][NH2:29])[N:13]=2)=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.[C:40](O)(=O)[CH2:41][OH:42].C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C.C(O)(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:40]([CH2:41][OH:42])[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

생성물 1

HCID 59472958{8-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 3-4 (5 g, 13 mMol), HOBT (1.9 g, 14.3 mMol), and glycolic acid (1.2 g, 15.6 mMol) in anhydrous DMF (100 mL) was added EDC (2.7 g, 14.3 mMol). The solution was stirred overnight at ambient temperature. The solution was then treated with 5 mL of glacial acetic acid and was heated to 80° C. in an oil bath for 2 hours. Upon cooling to room temperature, the reaction was diluted with ethyl acetate and washed with NaHCO3 (aq), water, and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo to yield 14-1 as a red solid. LC/MS (M+1) calculated: 425.5; observed: 425.6

후처리

  1. temperaturewas heated to 80° C. in an oil bath for 2 hours
  2. temperatureUpon cooling to room temperature
  3. washwashed with NaHCO3 (aq), water, and brine
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0bdbee5f9a564cfc82009b91521ade84
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008317B2

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