4-(1-Pyrrolidinyl)piperidine → 4-Pyridin-3-yl-2-[6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyrimidin-4-yl]-1,2-dihydro-3H-pyrazol-3-one dihydrochloride

HRID 37902

反応式

HRID 37902 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.[N:20]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1>[ClH:1].[ClH:1].[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:11]2[C:12](=[O:13])[N:8]([C:4]3[CH:3]=[C:2]([N:28]4[CH2:29][CH2:30][CH:25]([N:20]5[CH2:24][CH2:23][CH2:22][CH2:21]5)[CH2:26][CH2:27]4)[N:7]=[CH:6][N:5]=3)[NH:9][CH:10]=2)[CH:15]=1

参加物

4

反応物 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

生成物 1

HCID 688068394-Pyridin-3-yl-2-[6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyrimidin-4-yl]-1,2-dihydro-3H-pyrazol-3-one dihydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

100 mg (0.4 mmol) of the compound from Example 23 and 113 mg (0.7 mmol) of 4-pyrrolidin-1-ylpiperidine are initially charged in 3 ml of THF. The reaction mixture is reacted in a single-mode microwave oven (Emrys Optimizer) at 120° C. for 24 min. The cooled reaction solution is then concentrated on a rotary evaporator, and the residue is chromatographed by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). 1 ml of a 4 N solution of hydrogen chloride in dioxane is added to the resulting formate salt of the target compound, and the mixture is stirred at RT for 30 min. The suspension is then concentrated under reduced pressure, and the residue is dried.

後処理

  1. customThe reaction mixture is reacted in a single-mode microwave oven (Emrys Optimizer) at 120° C. for 24 min
  2. customThe cooled reaction solution
  3. concentrationis then concentrated on a rotary evaporator
  4. customthe residue is chromatographed by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
  5. addition1 ml of a 4 N solution of hydrogen chloride in dioxane is added to the resulting formate salt of the target compound
  6. concentrationThe suspension is then concentrated under reduced pressure
  7. customthe residue is dried

出典と根拠

ORDレコード
ord-11bb11dbb770472e9a9d318e8cf83859
出典データセット
uspto-grants-2013_09
特許番号
US08524699B2

関連ノート

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