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

HRID 1526237노트

반응식

HRID 1526237 반응식
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]

참가 물질

4

반응물 1

HCID 117667385HCID 117667385, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cc20a11323464236b661d057f7b9fcc5
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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