(5-(Methylsulfanyl)pyridin-3-yl)boronic acid → N-(6-(5-(Methylthio)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162439Notes

Reaction equation

HRID 1162439 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:47]1[CH:48]=[C:49](B(O)O)[CH:50]=[N:51][CH:52]=1>>[CH3:45][S:46][C:47]1[CH:48]=[C:49]([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:50]=[N:51][CH:52]=1

Participants

4

Reactant 3

HCID 22392014(5-(Methylsulfanyl)pyridin-3-yl)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 44124750N-(6-(5-(Methylthio)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Procedure

Following the procedure described for 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) (0.075 g, 0.36 mmol) was reacted with 5-(methylthio)pyridin-3-ylboronic acid (0.11 g, 0.64 mmol, Combi-Blocks, San Diego, Calif.) to afford the title compound as a white solid. MS (ESI positive ion) m/z: 300 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.94 (s, 1H), 9.00 (d, J=2.0 Hz, 1H), 8.60 (d, J=2.2 Hz, 1H), 8.34 (s, 1H), 8.27 (t, J=2.2 Hz, 1H), 8.12 (d, J=9.4 Hz, 1H), 7.90 (d, J=9.4 Hz, 1H), 2.64 (s, 3H), 2.12 (s, 3H).

Sources & evidence

ORD record
ord-755ac359be064e9abe9e79fd9c1300e0
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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