Diisopropylethylamine → 2-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid [2-methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

HRID 470355ノート

反応式

HRID 470355 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[NH:17][C:18]2[CH:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[CH:21][C:19]=2[N:20]=1.Cl.Cl.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([N:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2)[CH:35]=[CH:34][C:33]=1[NH2:45].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([N:38]2[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]2)[CH:35]=[CH:34][C:33]=1[NH:45][C:25]([C:23]1[CH:22]=[CH:21][C:19]2[N:20]=[C:16]([C:3]3[CH:4]=[C:5]([C:8]4[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=4)[CH:6]=[CH:7][C:2]=3[OH:1])[NH:17][C:18]=2[CH:24]=1)=[O:26]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686686372-Methoxy-4-(4-methylpiperazin-1-yl)aniline dihydrochlorideHCID 1361063252-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid

生成物 1

HCID 1361062932-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid [2-methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-amide収率 46.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-[2-hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid (containing 1 equivalent of DMA, 44 mg, 0.1 mmol), 2-methoxy-4-(4-methyl-piperazin-1-yl)-phenylamine di HCl salt (29.4 mg, 0.1 mmol) and HATU (38 mg, 0.1 mmol) in DMF (1.2 mL) was added DIEA (45 mg, 0.35 mmol). The reaction mixture was stirred at room temperature for 2 h and heated at 60° C. for 3 h, and then evaporated under reduced pressure. The residue was diluted with DMSO (1.5 mL), filtered and then purified with using HPLC (TFA/H2O/CH3CN) to afford the title compound (26.4 mg, 39%). ESI-MS m/z 565.5 (MH+).

後処理

  1. temperatureheated at 60° C. for 3 h
  2. customevaporated under reduced pressure
  3. additionThe residue was diluted with DMSO (1.5 mL)
  4. filtrationfiltered
  5. custompurified with using HPLC (TFA/H2O/CH3CN)

出典と根拠

ORDレコード
ord-e4b4fe006dc647a0bcfdff9fa9fad52a
出典データセット
uspto-grants-2014_01
特許番号
US08629147B2

反応ノート

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