HCID 86710713, compound → HCID 136377176, compound

HRID 1027286Notes

Reaction equation

HRID 1027286 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([OH:13])[C:10]([C:14]2[N:15]=[N:16][C:17]([O:20][CH:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]3)=[CH:18][CH:19]=2)=[C:9]([F:31])[CH:8]=1)(=O)=[O:4].CC1(C)C(C)(C)OB([C:42]2[CH:43]=[N:44][N:45](C([O-])=O)[CH:46]=2)O1>>[OH2:4].[F:31][C:9]1[C:10]([C:14]2[N:15]=[N:16][C:17]([O:20][CH:21]3[CH2:22][C:23]([CH3:30])([CH3:29])[NH:24][C:25]([CH3:27])([CH3:28])[CH2:26]3)=[CH:18][CH:19]=2)=[C:11]([OH:13])[CH:12]=[C:7]([C:42]2[CH:43]=[N:44][NH:45][CH:46]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 86710713HCID 86710713, compoundHCID 136377175HCID 136377175, compound

Product 1

HCID 136377176HCID 136377176, compound

Procedure

Following the representative procedure GENERAL METHOD 1-6 for Suzuki cross-coupling, 3-fluoro-5-hydroxy-4-(6-((2,2,6,6-tetramethylpiperidin-4-yl)oxy)pyridazin-3-yl)phenyl trifluoromethanesulfonate and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate were reacted and the crude product was purified via reverse phase preparative HPLC (10% CH3CN to 30% in H2O). After salt formation, the hydrochloride salt of 3-fluoro-5-(1H-pyrazol-4-yl)-2-(6-((2,2,6,6-tetramethylpiperidin-4-yl)oxy)pyridazin-3-yl)phenol hydrate was afforded as a yellow solid (49 mg, 25%). LCMS Rt=0.49 min; [M+H]: 412.3; 1H NMR (400 MHz, MeOD) δ 8.51 (d, J=9.5 Hz, 1H), 8.26 (s, 2H), 7.87 (d, J=9.5 Hz, 1H), 7.21 (dd, J=12.0, 1.5 Hz, 1H), 7.16 (s, 1H), 5.77 (tt, J=10.5, 4.0 Hz, 1H), 2.52 (dd, J=14.0, 4.0 Hz, 2H), 1.93 (dd, J=14.0, 10.5 Hz, 2H), 1.64 (s, 6H), 1.59 (s, 6H).

Workup

  1. customwere reacted
  2. customthe crude product was purified via reverse phase preparative HPLC (10% CH3CN to 30% in H2O)

Sources & evidence

ORD record
ord-73d9f1a4a80045c58e84459fae6fdb01
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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