Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-4-methyl-2-(methyloxy)benzamide

HRID 42246

反応式

HRID 42246 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.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.[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:56]=[C:57]([NH2:64])[C:58]4[CH:59]=[N:60][NH:61][C:62]=4[CH:63]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1>CN(C=O)C>[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:63]=[C:62]4[C:58]([CH:59]=[N:60][NH:61]4)=[C:57]([NH:64][C:6](=[O:8])[C:5]4[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=4[O:11][CH3:12])[CH:56]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 5971642-Methoxy-4-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

生成物 1

HCID 44540223N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-4-methyl-2-(methyloxy)benzamide収率 16.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-methyl-2-(methyloxy)benzoic acid (67 mg, 0.40 mmol) in DMF (1 ml) were added HATU (248 mg, 0.40 mmol) and DIPEA (0.211 mL, 1.21 mmol). The mixture was stirred for 30 mins under nitrogen before addition of 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.201 mmol). The reaction was stirred for 2 h then it was loaded onto PS-aminopropyl cartridge (5 g) and left for 3 h. The cartridge was washed with 10% MeOH in DCM. Appropriate fractions were combined and the solvent was evaporated. The residue was dissolved in MeOH: DMSO (1 ml; 1:1, v/v) and purified by Mass Directed Automated Preparative HPLC using method B. Solvent was evaporated under a stream of nitrogen to give title compound (13 mg).

後処理

  1. waitleft for 3 h
  2. washThe cartridge was washed with 10% MeOH in DCM
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in MeOH
  5. custom1:1, v/v) and purified by Mass Directed Automated Preparative HPLC
  6. customSolvent was evaporated under a stream of nitrogen

出典と根拠

ORDレコード
ord-f3a738058af44b96a6d517d617084b40
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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