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Diisopropylethylamine → 2-[6-(3,3-Difluoroazetidin-1-yl)pyrimidin-4-yl]-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one hydrochloride

HRID 37910
ノート
印刷プレビュー

反応式

HRID 37910 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][NH:9]2)[CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[F:30][C:31]1([F:35])[CH2:34][NH:33][CH2:32]1>C(O)C>[ClH:1].[F:30][C:31]1([F:35])[CH2:34][N:33]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([N:8]3[C:12](=[O:13])[C:11]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)=[CH:10][NH:9]3)[CH:3]=2)[CH2:32]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

生成物 1

HCID 708727812-[6-(3,3-Difluoroazetidin-1-yl)pyrimidin-4-yl]-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one hydrochloride

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

100 mg (0.4 mmol) of the compound from Example 23, 94 mg (0.7 mmol) of N,N-diisopropylethylamine and 95 mg (0.731 mmol) of 3,3-difluoroazetidine hydrochloride are suspended in 3 ml of ethanol and reacted at 120° C. in a single-mode microwave oven (CEM Explorer) for 40 min. The solvent is then removed, and the residue is taken up in 6 ml of DMSO. Undissolved components are removed by filtration, and the solution obtained is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product-containing fractions are combined and concentrated on a rotary evaporator, and the residue is dried under high vacuum. The residue is then stirred in 5 ml of a 4 N solution of hydrogen chloride in dioxane for 30 min. The solid is filtered off, washed with tert-butyl methyl ether and dried under high vacuum.

後処理

  1. customreacted at 120° C. in a single-mode microwave oven (CEM Explorer) for 40 min
  2. customThe solvent is then removed
  3. customUndissolved components are removed by filtration
  4. customthe solution obtained
  5. customis purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
  6. concentrationconcentrated on a rotary evaporator
  7. customthe residue is dried under high vacuum
  8. filtrationThe solid is filtered off
  9. washwashed with tert-butyl methyl ether
  10. customdried under high vacuum

出典と根拠

ORDレコード
ord-850c31b799284b4293d5c40f3752ee2b
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524699B2

反応ノート

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