Piperidine → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone

HRID 551596노트

반응식

HRID 551596 반응식
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][N:6]=1)=[O:4].COC([C:22]1[CH:27]=[N:26][C:25](C=O)=[CH:24][N:23]=1)=O.N1CC[CH2:33][CH2:32][CH2:31]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH:32]([N:23]1[CH2:22][CH2:27][N:26]([C:3]([C:5]2[CH:10]=[N:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:7][N:6]=2)=[O:4])[CH2:25][CH2:24]1)([CH3:33])[CH3:31]

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 44515461Methyl 5-formylpyrazine-2-carboxylateHCID 445157725-Piperidin-1-ylmethyl-pyrazine-2-carboxylic acid methyl ester

생성물 1

HCID 11544498(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone수율 23%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Piperidin-1-ylmethyl-pyrazine-2-carboxylic acid methyl ester. A mixture of 5-formyl-pyrazine-2-carboxylic acid methyl ester (0.400 g, 2.40 mmol), piperidine (0.204 g, 2.40 mmol), and NaB(OAc)3H (1.40 g, 3.60 mmol) in DCM (10 mL) was stirred for 18 h at rt. The reaction was quenched by the addition of 10% aq. NaOH (10 mL) and the mixture was stirred for 30 min. The mixture was extracted with DCM (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to yield the title compound (0.130 g, 23%).

후처리

  1. customThe reaction was quenched by the addition of 10% aq. NaOH (10 mL)
  2. stirringthe mixture was stirred for 30 min
  3. extractionThe mixture was extracted with DCM (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0b6bdcabb8e64553bf4cfa5ac1e27b03
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947718B2

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