Triethylamine → (R)-3-Oxo-3-(3-(2-(2-oxo-1,2-dihydropyridin-3-ylamino)pyrimidin-4-ylamino) piperidin-1-yl)propanenitrile

HRID 574004노트

반응식

HRID 574004 반응식
C(N(CC)CC)C.O=C1CCC(=O)N1[O:15][C:16](=O)[CH2:17][C:18]#[N:19].[NH:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:27][C:28]2[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]3[C:36](=[O:41])[NH:37][CH:38]=[CH:39][CH:40]=3)[N:29]=2)[CH2:22]1>ClCCl>[O:15]=[C:16]([N:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:27][C:28]2[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]3[C:36](=[O:41])[NH:37][CH:38]=[CH:39][CH:40]=3)[N:29]=2)[CH2:22]1)[CH2:17][C:18]#[N:19]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 534158962,5-Dioxopyrrolidin-1-yl 2-cyanoacetateHCID 71245038(R)-3-(4-(piperidin-3-ylamino)pyrimidin-2-ylamino)pyridin-2(1H)-one

생성물 1

HCID 71245122(R)-3-Oxo-3-(3-(2-(2-oxo-1,2-dihydropyridin-3-ylamino)pyrimidin-4-ylamino) piperidin-1-yl)propanenitrile수율 13.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (33 μL, 0.24 mmol) and 3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropane nitrile (prepared as described in BE875054(A1), 51 mg, 0.28 mmol) were added to a solution of (R)-3-(4-(piperidin-3-ylamino)pyrimidin-2-ylamino)pyridin-2(1H)-one (Preparation 19c, 67 mg, 0.23 mmol) in dichloromethane (3 mL). The reaction mixture was stirred at ambient temperature for 24 hours and solvent was evaporated. Water was added and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4), evaporated under reduced pressure and the residue was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (11 mg, 12%) as a solid.

후처리

  1. customsolvent was evaporated
  2. additionWater was added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customthe residue was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid

출처 및 근거

ORD 기록
ord-b96213d4a58e4316b284eab2551e95e9
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034311B2

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