Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-3-methyl-2-(methyloxy)benzamide

HRID 42249

반응식

HRID 42249 반응식
[CH3:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=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:5](=[O:7])[C:4]4[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=4[O:11][CH3:12])[CH:56]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9523962-Methoxy-3-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

생성물 1

HCID 44540309N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-3-methyl-2-(methyloxy)benzamide수율 3.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DMF (1 ml) was added to 3-methyl-2-(methyloxy)benzoic acid (134 mg, 0.81 mmol) (Apin Chemicals), HATU (306 mg, 0.81 mmol) and DIPEA (0.422 ml, 2.417 mmol). The reaction was stirred for 30 mins under nitrogen before addition of 6-(1H-indol-4-yl)-1H-indazol-4-amine (100 mg, 0.403 mmol). The reaction was stirred under nitrogen at RT overnight, 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 (2 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 to give title compound (6 mg).

후처리

  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

출처 및 근거

ORD 기록
ord-10cbc3aef8de4be1864a6886405e152c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536169B2

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