Thiophenol → HCID 136253085, compound

HRID 1027233Notes

Reaction equation

HRID 1027233 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[CH:6]=[C:5]([O:14]C)[C:4]=1[C:16]1[N:21]=[N:20][C:19]([N:22]([CH3:33])[CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)=[CH:18][CH:17]=1.C1(S)C=CC=CC=1>>[CH3:33][N:22]([CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)[C:19]1[N:20]=[N:21][C:16]([C:4]2[C:5]([OH:14])=[CH:6][C:7]([C:9]3[CH:13]=[N:12][NH:11][CH:10]=3)=[CH:8][C:3]=2[OH:2])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 7969ThiophenolHCID 86710638HCID 86710638, compound

Product 1

HCID 136253085HCID 136253085, compound

Procedure

From compound 6-(2,6-dimethoxy-4-(1H-pyrazol-4-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (43 mg, 0.095 mmol), following GENERAL METHOD 3-1 for methoxy deprotection using thiophenol (22.1 mg, 0.2 mmol), compound 2-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-5-(1H-pyrazol-4-yl)benzene-1,3-diol was afforded as a pale yellow solid (20 mg, 45% yield) after HPLC purification. LCMS Rt=0.41 min [Method Q], MS (M+1)=423.3. 1H NMR (METHANOL-d4) δ 8.60 (d, J=10.1 Hz, 1H), 7.91 (s, 2H), 7.20 (d, J=10.1 Hz, 1H), 6.66 (s, 2H), 5.01 (t, J=12.4 Hz, 1H), 2.90-3.01 (m, 3H), 1.64-1.73 (m, 2H), 1.52-1.61 (m, 2H), 1.38 (s, 6H), 1.23 (s, 6H).

Sources & evidence

ORD record
ord-4f89cacdd3d14832813454407891f3ac
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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