3-(Methylthio)benzeneboronic acid → N-(6-(3-(Methylthio)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162440Notes

Reaction equation

HRID 1162440 reaction equation
CC1C=CC(S(N[C:12]2[CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]4[N:22]([CH:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[N:26]=4)[N:23]=3)[CH:15]=[CH:16][CH:17]=2)(=O)=O)=CC=1.ClC1C=CC2N(C=C(NC(=O)C)N=2)N=1.[CH3:45][S:46]C1C=C(B(O)O)C=CC=1>>[CH3:45][S:46][C:12]1[CH:13]=[C:14]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([CH:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[N:26]=3)[N:23]=2)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 27343833-(Methylthio)benzeneboronic 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 44124751N-(6-(3-(Methylthio)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

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) (0.075 g, 0.36 mmol) was reacted with 3-(methylthio)phenylboronic acid (0.11 g, 0.64 mmol, Alfa Aesar, Ward Hill, Mass.) to afford the title compound as a yellow solid. MS (ESI positive ion) m/z: 299 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.91 (s, 1H), 8.30 (s, 1H), 8.06 (d, J=9.6 Hz, 1H), 7.90 (s, 1H), 7.80-7.82 (m, 2H), 7.49 (t, J=7.8 Hz, 1H), 7.40-7.42 (m, 1H), 2.57 (s, 3H), 2.11 (s, 3H).

Sources & evidence

ORD record
ord-de02c8c0fddf4836bee51d9b5e5267cb
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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