Thiophenol → 5-(Imidazo[1,2-a]pyrazin-3-yl)-2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenol

HRID 1027300Notes

Reaction equation

HRID 1027300 reaction equation
C1(S)C=CC=CC=1.[N:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:28]=[N:27][C:26]([N:29]([CH3:40])[CH:30]4[CH2:35][C:34]([CH3:37])([CH3:36])[NH:33][C:32]([CH3:39])([CH3:38])[CH2:31]4)=[CH:25][CH:24]=3)=[C:19]([O:41]C)[CH:18]=2)[N:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=12.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[N:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:28]=[N:27][C:26]([N:29]([CH3:40])[CH:30]4[CH2:35][C:34]([CH3:36])([CH3:37])[NH:33][C:32]([CH3:39])([CH3:38])[CH2:31]4)=[CH:25][CH:24]=3)=[C:19]([OH:41])[CH:18]=2)[N:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=12

Participants

5

Reactant 3

HCID 7969Thiophenol2×HCID 11430Potassium CarbonateHCID 867107286-(4-(imidazo[1,2-a]pyrazin-3-yl)-2-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine

Product 1

HCID 1362530465-(Imidazo[1,2-a]pyrazin-3-yl)-2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenolYield 17.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following GENERAL METHOD 3-1 for methoxy deprotection using thiophenol, 6-(4-(imidazo[1,2-a]pyrazin-3-yl)-2-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (49 mg, 0.1 mmol) was treated with thiophenol (0.01 mL, 0.12 mmol) and K2CO3 (14 mg, 0.11 mmol) in NMP (2 mL) for 30 minutes at 190° C. to afford 5-(imidazo[1,2-a]pyrazin-3-yl)-2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenol (8 mg). MS: 458.4 [M+H+]; LCMS Rt=0.47 min [Method Q]; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.16 (s, 1H), 8.41 (d, J=5.05 Hz, 1H), 7.92-7.97 (m, 2H), 7.88 (d, J=10.11 Hz, 1H), 7.75 (d, J=8.08 Hz, 1H), 7.31 (s, 1H), 7.13 (s, 1H), 7.05 (d, J=9.60 Hz, 1H), 4.99 (br. s., 1H), 3.05 (s, 3H), 1.72 (d, J=12.13 Hz, 2H), 1.46 (t, J=12.38 Hz, 2H), 1.39 (s, 6H), 1.23 (s, 6H).

Sources & evidence

ORD record
ord-884580942438420b94998ee5917bd63b
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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