5-(Methylsulphonyl)pyridine-3-boronic acid → HCID 44124752, compound

HRID 1162441Notes

Reaction equation

HRID 1162441 reaction equation
CC1C=CC(S(NC2C=C(C3C=CC4N(C=C(NC(=O)C)N=4)N=3)C=CC=2)(=O)=O)=CC=1.Cl[C:32]1[CH:33]=[CH:34][C:35]2[N:36]([CH:38]=[C:39]([NH:41][C:42](=[O:44])[CH3:43])[N:40]=2)[N:37]=1.[CH3:45][S:46]([C:49]1[CH:50]=[C:51](B(O)O)[CH:52]=[N:53][CH:54]=1)(=[O:48])=[O:47]>>[CH3:45][S:46]([C:49]1[CH:50]=[C:51]([C:32]2[CH:33]=[CH:34][C:35]3[N:36]([CH:38]=[C:39]([NH:41][C:42](=[O:44])[CH3:43])[N:40]=3)[N:37]=2)[CH:52]=[N:53][CH:54]=1)(=[O:48])=[O:47]

Participants

4

Reactant 3

HCID 441193815-(Methylsulphonyl)pyridine-3-boronic acidHCID 44124523N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamideHCID 59519510N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide

Product 1

HCID 44124752HCID 44124752, compound

Procedure

Following the procedure described for compound N-(6-(3-(4-methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 1), N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (Example 1, Step 4) (0.084 g, 0.40 mmol) was reacted with 5-(methylsulfonyl)pyridin-3-ylboronic acid (0.14 g, 0.72 mmol, Combi-Blocks, San Diego, Calif.) to afford the title compound as a yellow solid. MS (ESI positive ion) m/z: 332 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.97 (s, 1H), 9.56 (d, J=2.2 Hz, 1H), 9.19 (d, J=2.2 Hz, 1H), 8.89 (t, J=2.2 Hz, 1H), 8.39 (s, 1H), 8.19 (d, J=9.4 Hz, 1H), 8.00 (d, J=9.4 Hz, 1H), 3.31 (s, 3H), 2.12 (s, 3H).

Sources & evidence

ORD record
ord-2b02f05f97f5456ea045ddc6c79b7af1
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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