1,2-Dichloroethane → 8-[4-(1,3-dioxolan-2-yl)phenyl]-3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678774ノート

反応式

HRID 1678774 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.[CH3:40][N:41]1[CH:45]=[C:44]([C:46](O)=O)[N:43]=[CH:42]1.C(Cl)CCl>CN(C=O)C.O.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:46]([C:44]5[N:43]=[CH:42][N:41]([CH3:40])[CH:45]=5)[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 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

生成物 1

HCID 594729458-[4-(1,3-dioxolan-2-yl)phenyl]-3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide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 1-methyl-1H-imidazole-4-carboxylic acid (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 24 mL of acetic acid and was heated to 80° C. in an oil bath for 5 hours. Upon cooling to room temperature, an equal volume of water was added and the resulting suspension was filtered and washed with copious amounts of water. The collected solid was dried azeotropically with toluene three times to yield 13-1 as a tan solid. Mass (M+1) calculated: 475.1877 observed: 475.1871

後処理

  1. temperaturewas heated to 80° C. in an oil bath for 5 hours
  2. temperatureUpon cooling to room temperature
  3. filtrationthe resulting suspension was filtered
  4. washwashed with copious amounts of water
  5. dry with materialThe collected solid was dried azeotropically with toluene three times

出典と根拠

ORDレコード
ord-436cf5f3f54c421ca59b53e27cb5dba5
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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