Thiophenol → 2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)phenol

HRID 1027297Notes

Reaction equation

HRID 1027297 reaction equation
C1(S)C=CC=CC=1.C[O:9][C:10]1[CH:15]=[C:14]([C:16]2[N:17]=[CH:18][N:19]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=2)[CH:13]=[CH:12][C:11]=1[C:29]1[N:34]=[N:33][C:32]([N:35]([CH3:46])[CH:36]2[CH2:41][C:40]([CH3:43])([CH3:42])[NH:39][C:38]([CH3:45])([CH3:44])[CH2:37]2)=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[CH3:46][N:35]([CH:36]1[CH2:37][C:38]([CH3:45])([CH3:44])[NH:39][C:40]([CH3:43])([CH3:42])[CH2:41]1)[C:32]1[N:33]=[N:34][C:29]([C:11]2[CH:12]=[CH:13][C:14]([C:16]3[N:17]=[CH:18][N:19]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:28])[CH3:26])[CH:20]=3)=[CH:15][C:10]=2[OH:9])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 7969Thiophenol2×HCID 11430Potassium CarbonateHCID 867107256-(2-methoxy-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine

Product 1

HCID 1363771822-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)phenol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following GENERAL METHOD 3-1 for methoxy deprotection using thiophenol, 6-(2-methoxy-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (50 mg, 0.09 mmol) was treated with thiophenol (0.01 mL, 0.11 mmol) and K2CO3 (12 mg, 0.09 mmol) in NMP (2 mL) for 30 minutes at 190° C. to afford 2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)phenol and an impurity (50 mg, MS: 537.6 [M+H+]).

Sources & evidence

ORD record
ord-df2be34129564d44a0c2a318428f7361
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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