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 1678777ノート

反応式

HRID 1678777 の反応式
[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

参加物

8

反応物 4

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

生成物 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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-0bdbee5f9a564cfc82009b91521ade84
出典データセット
uspto-grants-2011_08
特許番号
US08008317B2

反応ノート

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