1-Ethyl-3-methyl-1H-pyrazole-5-carboxylic acid → 1-Ethyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-methyl-1H-pyrazole-5-carboxamide

HRID 244733

반응식

HRID 244733 반응식
[CH2:1]([N:3]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([CH3:11])=[N:4]1)[CH3:2].F[P-](F)(F)(F)(F)F.CN(C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.[NH:36]1[C:44]2[C:39](=[C:40]([C:45]3[CH:46]=[C:47]([NH2:54])[C:48]4[CH:49]=[N:50][NH:51][C:52]=4[CH:53]=3)[CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37]1>CN(C=O)C.CCN(C(C)C)C(C)C>[CH2:1]([N:3]1[C:7]([C:8]([NH:54][C:47]2[CH:46]=[C:45]([C:40]3[CH:41]=[CH:42][CH:43]=[C:44]4[C:39]=3[CH:38]=[CH:37][NH:36]4)[CH:53]=[C:52]3[C:48]=2[CH:49]=[N:50][NH:51]3)=[O:10])=[CH:6][C:5]([CH3:11])=[N:4]1)[CH3:2]

참가 물질

6

반응물 3

HCID 27437941-Ethyl-3-methyl-1H-pyrazole-5-carboxylic 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 445401561-Ethyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-methyl-1H-pyrazole-5-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 81531Diisopropylethylamine용매

실험 절차

1-Ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (67.8 mg) was treated with N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (168 mg) in DMF (750 μl) and DIPEA (150 μl). Reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg) in DMF (350 μl). Reaction mixture was left to stand at 22° C. for 16 hrs. Solvent was removed in vacuo and the product re-dissolved in chloroform (0.3 ml) prior to application on to a preconditioned (methanol then chloroform) aminopropyl SPE cartridge (1 g). Product was eluted after 2 h with ethyl acetate:methanol (1:1, 3.2 ml), and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method B) gave the title compound.

후처리

  1. customReaction mixture
  2. customReaction mixture
  3. waitwas left
  4. waitto stand at 22° C. for 16 hrs
  5. customSolvent was removed in vacuo
  6. dissolutionthe product re-dissolved in chloroform (0.3 ml)
  7. washProduct was eluted after 2 h with ethyl acetate:methanol (1:1, 3.2 ml)
  8. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  9. customPurification by mass

출처 및 근거

ORD 기록
ord-5aafeaabfc944540b2cc041bafca5b9a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658635B2

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