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

HRID 574004ノート

反応式

HRID 574004 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b96213d4a58e4316b284eab2551e95e9
出典データセット
uspto-grants-2015_05
特許番号
US09034311B2

反応ノート

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