Azetidine → 2-(6-Azetidin-1-ylpyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

HRID 37908

反応式

HRID 37908 の反応式
Cl[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.[NH:20]1[CH2:23][CH2:22][CH2:21]1>C(O)C>[N:20]1([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)[CH2:23][CH2:22][CH2:21]1

参加物

4

反応物 2

HCID 10422AzetidineHCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

生成物 1

HCID 688044312-(6-Azetidin-1-ylpyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

150 mg (0.5 mmol) of the compound from Example 23 and 63 mg (1 l mmol) of azetidine are suspended in 4 ml of ethanol and reacted at 120° C. in a single-mode microwave oven (CEM Explorer) for 40 min. The solid is filtered off, washed twice with in each case 0.5 ml of ethanol and discarded. The mother liquor is combined with the wash solutions, and the solvent is removed on a rotary evaporator. The residue 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. The residue is stirred under reflux in ethanol for 20 min and then filtered off while still hot. The solid obtained is dried under high vacuum.

後処理

  1. customreacted at 120° C. in a single-mode microwave oven (CEM Explorer) for 40 min
  2. filtrationThe solid is filtered off
  3. washwashed twice with in each case 0.5 ml of ethanol
  4. customthe solvent is removed on a rotary evaporator
  5. customThe residue is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
  6. concentrationconcentrated on a rotary evaporator
  7. temperatureunder reflux in ethanol for 20 min
  8. filtrationfiltered off while still hot
  9. customThe solid obtained
  10. customis dried under high vacuum

出典と根拠

ORDレコード
ord-94efd4b69ae0467ba2f7f24227b8fbd3
出典データセット
uspto-grants-2013_09
特許番号
US08524699B2

関連ノート

読み込み中…