5-methyl-1H-pyrazole-3-carboxylic acid → HCID 44540242, 화합물

HRID 244717

반응식

HRID 244717 반응식
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.F[P-](F)(F)(F)(F)F.CN(C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.[NH:34]1[C:42]2[C:37](=[C:38]([C:43]3[CH:44]=[C:45]([NH2:58])[C:46]4[C:50]([CH:51]=3)=[N:49][N:48](C3CCCCO3)[CH:47]=4)[CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35]1>CN(C=O)C.CCN(C(C)C)C(C)C>[NH:34]1[C:42]2[C:37](=[C:38]([C:43]3[CH:51]=[C:50]4[C:46]([CH:47]=[N:48][NH:49]4)=[C:45]([NH:58][C:7]([C:4]4[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=4)=[O:9])[CH:44]=3)[CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35]1

참가 물질

6

반응물 3

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

생성물 1

HCID 44540242HCID 44540242, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 81531Diisopropylethylamine용매

실험 절차

5-Methyl-1H-pyrazole-3-carboxylic acid (10 mg) in DMF (0.2 ml) was treated with N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (27 mg) in DMF (0.2 ml) and DIPEA (0.03 ml). The reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (20 mg) in DMF (0.2 ml). The reaction mixture was shaken for five min and left to stand at 22° C. for 18 h. The solvent was removed in vacuo and the product re-dissolved in methanol (1 ml) prior to application on to an SCX SPE cartridge (1 g). The product was eluted after 1 h with 2M ammonia in methanol (2×3 ml), the fractions were combined and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) afforded the title compound.

후처리

  1. stirringThe reaction mixture was shaken for five min
  2. waitleft
  3. waitto stand at 22° C. for 18 h
  4. customThe solvent was removed in vacuo
  5. dissolutionthe product re-dissolved in methanol (1 ml)
  6. washThe product was eluted after 1 h with 2M ammonia in methanol (2×3 ml)
  7. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  8. customPurification by mass

출처 및 근거

ORD 기록
ord-222ac297bb7d4c768557abf89a2cb8ca
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658635B2

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