1,2-Dichloroethane → 3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678773ノート

反応式

HRID 1678773 の反応式
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[NH:30][C:29]([C:31]5[N:36]=[CH:35][CH:34]=[CH:33][N:32]=5)=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].C1C=CC2N(O)N=NC=2C=1.[CH3:53][N:54]1[CH:58]=[C:57]([C:59](O)=O)[N:56]=[CH:55]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(O)(=O)C>[CH3:53][N:54]1[CH:58]=[C:57]([C:59]2[N:12]3[C:3]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[C:7]([C:13]5[CH:18]=[CH:17][C:16]([CH2:19][N:20]6[CH2:21][CH2:22][CH:23]([C:26]7[NH:30][C:29]([C:31]8[N:36]=[CH:35][CH:34]=[CH:33][N:32]=8)=[N:28][N:27]=7)[CH2:24][CH2:25]6)=[CH:15][CH:14]=5)=[N:8][C:9]=4[CH:10]=[CH:11]3)=[N:1][N:2]=2)[N:56]=[CH:55]1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 178514342HCID 178514342、化合物

生成物 1

HCID 1784812663-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 11-3 (0.23 g, 0.4 mMol), HOBT (0.06 g, 0.45 mMol), and 1-methyl-1H-imidazole-4-carboxylic acid (0.06 g, 0.45 mMol) in anhydrous DMF (2 mL) was added DIEA (0.13 mL, 0.8 mMol) followed by EDC (0.09 g, 0.5 mMol). The solution was heated in the microwave reactor for 15 minutes at 80° C. Solution was then treated with 0.2 mL of acetic acid and was heated to 80° C. in the microwave reactor for 20 minutes. Upon cooling to room temperature, the solution was passed through a syringe filter and purified on a C18 reverse phase HPLC to give 12-1 as a solid. Mass (M+1) calculated: 632.2742 observed: 632.274

後処理

  1. temperaturewas heated to 80° C. in the microwave reactor for 20 minutes
  2. temperatureUpon cooling to room temperature
  3. customthe solution was passed through a syringe
  4. filtrationfilter
  5. custompurified on a C18 reverse phase HPLC

出典と根拠

ORDレコード
ord-bf05e73271d44b21928093b65535d432
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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