6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine → HCID 86710657, compound

HRID 1027250Notes

Reaction equation

HRID 1027250 reaction equation
[CH3:1][O:2][C:3]1[C:4](B(O)O)=[CH:5][C:6]2[N:10]=[C:9]([CH3:11])[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=2[CH:20]=1.Cl[C:25]1[N:30]=[N:29][C:28]([N:31]([CH3:42])[CH:32]2[CH2:37][C:36]([CH3:39])([CH3:38])[NH:35][C:34]([CH3:41])([CH3:40])[CH2:33]2)=[CH:27][CH:26]=1>>[CH3:1][O:2][C:3]1[C:4]([C:25]2[N:30]=[N:29][C:28]([N:31]([CH3:42])[CH:32]3[CH2:37][C:36]([CH3:38])([CH3:39])[NH:35][C:34]([CH3:41])([CH3:40])[CH2:33]3)=[CH:27][CH:26]=2)=[CH:5][C:6]2[N:10]=[C:9]([CH3:11])[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=2[CH:20]=1

Participants

3

Reactant 2

HCID 867105396-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amineHCID 86710658HCID 86710658, compound

Product 1

HCID 86710657HCID 86710657, compoundYield 89%

Procedure

The mixture of (6-methoxy-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-5-yl)boronic acid and the pinacol ester (78 mg, 0.139 mmol), and Intermediate 1-1 (26 mg, 0.092 mmol) were reacted according to GENERAL METHOD 1-5 for Suzuki coupling. 6-(6-Methoxy-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-5-yl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine was obtained after flash column chromatography purification (44 mg, 89% yield). MS (M+1)=539.7.

Sources & evidence

ORD record
ord-8b929190e60e4a4da1aebb6b07e076ed
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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