6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine → HCID 86710685, compound

HRID 1027271Notes

Reaction equation

HRID 1027271 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1B1OC(C)(C)C(C)(C)O1)[C:9]1=[CH:22][N:23]=[CH:24][N:8]1[CH2:7][CH2:6]2.Cl[C:26]1[N:31]=[N:30][C:29]([N:32]([CH3:43])[CH:33]2[CH2:38][C:37]([CH3:40])([CH3:39])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]2)=[CH:28][CH:27]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:26]1[N:31]=[N:30][C:29]([N:32]([CH3:43])[CH:33]3[CH2:38][C:37]([CH3:39])([CH3:40])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]3)=[CH:28][CH:27]=1)[C:9]1=[CH:22][N:23]=[CH:24][N:8]1[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 867105396-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine2×HCID 86710686HCID 86710686, compound

Product 1

HCID 86710685HCID 86710685, compoundYield 98%

Procedure

Following standard GENERAL METHOD 1-4 for Suzuki coupling using 8-methoxy-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydroimidazo[5,1-a]isoquinoline (104 mg, 0.32 mmol) and 6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (Intermediate 1-1, 90 mg, 0.32 mmol), afforded 6-(8-methoxy-5,6-dihydroimidazo[5,1-a]isoquinolin-9-yl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (140 mg) MS [M+H+]=447.6.

Sources & evidence

ORD record
ord-22f8c51ae1294ab58eb50b99e97d74f5
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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