Ammonia → N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-1H-benzimidazole-2-carboxamide

HRID 42245

反応式

HRID 42245 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.[NH:13]1[C:21]2[C:16](=[C:17]([C:22]3[CH:23]=[C:24]([NH2:37])[C:25]4[C:29]([CH:30]=3)=[N:28][N:27](C3CCCCO3)[CH:26]=4)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.CCN(C(C)C)C(C)C.N>CN(C=O)C.CO>[NH:13]1[C:21]2[C:16](=[C:17]([C:22]3[CH:30]=[C:29]4[C:25]([CH:26]=[N:27][NH:28]4)=[C:24]([NH:37][C:10]([C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[O:12])[CH:23]=3)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

参加物

7

反応物 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

生成物 1

HCID 44540221N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-1H-benzimidazole-2-carboxamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

1H-Benzimidazole-2-carboxylic acid (available from Apollo Scientific, 25 mg, 0.151 mmol), O-(7-Azabenzatriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (63 mg, 0.17 mmol) and 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg, 0.15 mmol) were dissolved in anhydrous DMF (3 ml) and then treated with DIPEA (0.05 ml, 0.30 mmol). The reactions were then stirred at room temperature for 15 hours. The mixture was treated with methanol (3 ml) and then Macroporous-Tosic Acid (170 mg, 0.75 mmol) then stirred for 15 hours. The mixture was then treated with 0.88 ammonia solution (0.60 ml), stirred for 10 minutes, then filtered and solvent blown off under a stream of nitrogen. The crude residue was purified by Mass Directed Automated Preparative HPLC (Method B) to give after evaporation of solvents the title compound as a yellow solid (27 mg). LCMS (Method B) m/z 393 [MH+], Rt=1.04 min.

後処理

  1. stirringstirred for 10 minutes
  2. filtrationfiltered
  3. customThe crude residue was purified by Mass Directed Automated Preparative HPLC (Method B)
  4. customto give
  5. customafter evaporation of solvents the title compound as a yellow solid (27 mg)

出典と根拠

ORDレコード
ord-faf48123d94743ae808c61a29cfd745c
出典データセット
uspto-grants-2013_09
特許番号
US08536169B2

関連ノート

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