4-(Benzylamino)but-3-en-2-one → 2-[(3-acetyl-1-benzyl-4H-pyridin-4-yl)methyl]-6-methoxy-tetralin-1-one

HRID 2207160Notes

Reaction equation

HRID 2207160 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:14]/[CH:15]=[CH:16]/[CH:17]=O)[CH2:7][CH2:6]2.[CH2:19]([NH:26][CH:27]=[CH:28][C:29](=[O:31])[CH3:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:29]([C:28]1[CH:15]([CH2:14][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]2=[O:13])[CH:16]=[CH:17][N:26]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=1)(=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 5214434-(Benzylamino)but-3-en-2-oneHCID 90303875(E)-4-(6-methoxy-1-oxo-tetralin-2-yl)but-2-enal

Product 1

HCID 1185580502-[(3-acetyl-1-benzyl-4H-pyridin-4-yl)methyl]-6-methoxy-tetralin-1-one

Procedure

The title compound 52 is prepared according to the procedure reported in step D of Example 8 with aldehyde 54 (100 mg, 0.41 mmol) and enamine 30 (70 mg, 0.4 mmol) as reactants. Purification by column chromatography on SiO2 (Petroleum 4/EtOAc=4:1) afford the title compound 52 as a yellow oil. (Yield 55.0 mg, 35%).

Workup

  1. customThe title compound 52 is prepared
  2. customPurification by column chromatography on SiO2 (Petroleum 4/EtOAc=4:1)

Sources & evidence

ORD record
ord-3316a983497d437799059e4eeda23c09
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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