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

HRID 2207168Notes

Reaction equation

HRID 2207168 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.[C:19]1([CH3:32])[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH:26][CH:27]=[CH:28][C:29](=[O:31])[CH3:30])[CH:20]=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]([CH2:25][C:21]2[CH:20]=[C:19]([CH3:32])[CH:24]=[CH:23][CH:22]=2)[CH:27]=1)(=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 903031764-(m-Tolylmethylamino)but-3-en-2-oneHCID 90303875(E)-4-(6-methoxy-1-oxo-tetralin-2-yl)but-2-enal

Product 1

HCID 1185580562-[[3-acetyl-1-(m-tolylmethyl)-4H-pyridin-4-yl]methyl]-6-methoxy-tetralin-1-one

Procedure

The title compound 61 is prepared according to the procedure reported in step D of Example 8 with aldehyde 54 (100 mg, 0.41 mmol) and enamine 62 (80 mg, 0.42 mmol) as reactants. Purification by column chromatography on SiO2 (Petroleum Ether/EtOAc=2:1) afford the title compound 61 as a yellow solid. (Yield 115 mg, 68%).

Workup

  1. customThe title compound 61 is prepared
  2. customPurification by column chromatography on SiO2 (Petroleum Ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-38e652ba76ea4f5c8c41dbdec453b3a5
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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