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

HRID 1027294Notes

Reaction equation

HRID 1027294 reaction equation
C1(S)C=CC=CC=1.[NH:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[N:23][C:22]([N:25]([CH3:36])[CH:26]3[CH2:31][C:30]([CH3:33])([CH3:32])[NH:29][C:28]([CH3:35])([CH3:34])[CH2:27]3)=[CH:21][CH:20]=2)=[C:15]([O:37]C)[CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[NH:10]1[CH:11]=[CH:12][N:8]=[C:9]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[N:23][C:22]([N:25]([CH3:36])[CH:26]3[CH2:31][C:30]([CH3:32])([CH3:33])[NH:29][C:28]([CH3:35])([CH3:34])[CH2:27]3)=[CH:21][CH:20]=2)=[C:15]([OH:37])[CH:14]=1

Participants

5

Reactant 3

HCID 7969Thiophenol2×HCID 11430Potassium CarbonateHCID 867107226-(4-(1H-imidazol-2-yl)-2-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine

Product 1

HCID 1362530325-(1H-imidazol-2-yl)-2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenolYield 14.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following GENERAL METHOD 3-1 for methoxy deprotection using thiophenol, 6-(4-(1H-imidazol-2-yl)-2-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (40 mg, 0.1 mmol) was treated with thiophenol (0.01 mL, 0.11 mmol) and K2CO3(13 mg, 0.1 mmol) in NMP (2 mL) for 30 min at 190° C. to afford 5-(1H-imidazol-2-yl)-2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenol as pale yellow powder (6 mg). MS: 407.4 [M+H+]; LCMS Rt=0.40 min [Method Q]; 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.00 (d, J=10.11 Hz, 1H), 7.68-7.78 (m, 1H), 7.32-7.41 (m, 2H), 7.19 (d, J=10.11 Hz, 1H), 7.05 (s, 2H), 4.96 (br. s., 1H), 2.90 (s, 3H), 1.58 (dd, J=12.38, 3.28 Hz, 2H), 1.46 (t, J=12.38 Hz, 2H), 1.28 (s, 6H), 1.12 (s, 6H).

Sources & evidence

ORD record
ord-0a3807bc218d4c8d8264f7bfab3ebe55
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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