HCID 117667385、化合物 → 6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-[(2R)-pyrrolidin-2-ylmethoxy]pyrazine-2-carboxamide

HRID 1526237ノート

反応式

HRID 1526237 の反応式
C([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[N:16]=[C:17]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]4)[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[C:18]([C:23]([NH2:25])=[O:24])=[N:19][C:20]=1[CH2:21][CH3:22])C1C=CC=CC=1>[Pd].C(O)(=O)C>[CH2:21]([C:20]1[N:19]=[C:18]([C:23]([NH2:25])=[O:24])[C:17]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]4)[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[N:16][C:15]=1[O:14][CH2:13][C@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[CH3:22]

参加物

4

反応物 1

HCID 117667385HCID 117667385、化合物

生成物 1

HCID 1176670436-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-[(2R)-pyrrolidin-2-ylmethoxy]pyrazine-2-carboxamide収率 88.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

To a mixture of 5-{[(2R)-1-benzylpyrrolidin-2-yl]methoxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (182 mg), and acetic acid (3 mL) was added 10% palladium-supported carbon (53% wet product) (63 mg), followed by stirring for 6 hours under a hydrogen gas atmosphere (4 atm). The reactant was filtered through celite, then the mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with a mixed solvent of chloroform:methanol=8:2. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=98:2) to obtain 6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-[(2R)-pyrrolidin-2-ylmethoxy]pyrazine-2-carboxamide (138 mg) as a yellow solid.

後処理

  1. filtrationThe reactant was filtered through celite
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additiona saturated aqueous sodium hydrogen carbonate solution was added
  4. extractionfollowed by extraction with a mixed solvent of chloroform
  5. washThe organic phase was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=98:2)

出典と根拠

ORDレコード
ord-cc20a11323464236b661d057f7b9fcc5
出典データセット
uspto-grants-2015_07
特許番号
US09085540B2

反応ノート

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