Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-(methyloxy)benzamide

HRID 42247

反応式

HRID 42247 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.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:7](=[O:9])[C:6]4[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=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 5201672-Methoxy-5-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 44540224N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-(methyloxy)benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-methyl-2-(methyloxy)benzoic acid (67 mg, 0.40 mmol) in DMF (1 ml), HATU (248 mg, 0.40 mmol) and DIPEA (156 mg, 1.208 mmol) were added. The reaction was stirred for 30 mins under nitrogen before addition of 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol). The reaction was stirred for 3 h then it was loaded onto a PS-aminopropyl cartridge 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. The solvent was dried under a stream of nitrogen. The residue was dissolved in DMSO and further purified by HPLC using the following conditions:

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. customThe solvent was dried under a stream of nitrogen
  7. dissolutionThe residue was dissolved in DMSO
  8. customfurther purified by HPLC

出典と根拠

ORDレコード
ord-418e8f9161d04a56b0b204662184b67a
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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