1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

HRID 251205

반응식

HRID 251205 반응식
[CH3:1][C:2]1[C:3]([CH:8]([NH2:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][CH2:24][CH:25]=O.[BH-](O[C:37]([CH3:39])=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[C:3]([CH:8]([N:10]([CH:39]2[C:37]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:3][CH2:8][CH2:9]2)[CH2:25][CH2:24][CH2:23][CH2:22][N:13]2[C:14](=[O:21])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]2=[O:11])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 457911661-(3-Methylpyridin-2-yl)ethan-1-amine

생성물 1

HCID 672725222-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of the above amine and 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (127 mg, 0.58 mmol) in CH2Cl2 (2.5 mL) was added NaBH(OAc)3 (117 mg, 0.55 mmol) and the reaction was stirred at room temperature under N2 for 16 hours. The mixture was diluted with saturated aqueous NaHCO3 (10 mL) and was extracted with CH2Cl2 (10 mL×3). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1) gave 2-{4-[[1-(3-methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione as a 1:1 mixture of two diastereomers (72 mg, 0.15 mmol, 43%) along with some single diastereomer (33 mg, 0.07 mmol, 20%).

후처리

  1. extractionwas extracted with CH2Cl2 (10 mL×3)
  2. dry with materialThe combined organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1)

출처 및 근거

ORD 기록
ord-f0f15f6ef15d4b0cb2055b86bf23ad42
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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