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ノート

反応式

HRID 244733 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 81531Diisopropylethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5aafeaabfc944540b2cc041bafca5b9a
出典データセット
uspto-grants-2014_02
特許番号
US08658635B2

反応ノート

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