3-Aminophenylboronic acid → N-(6-(3-Aminophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162436Notes

Reaction equation

HRID 1162436 reaction equation
CC1C=CC(S([NH:11][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.NC1C=C(B(O)O)C=CC=1>>[NH2:11][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 922693-Aminophenylboronic 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 57749413N-(6-(3-Aminophenyl)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) (0.071 g, 0.34 mmol) was reacted with 3-aminobenzeneboronic acid (0.094 g, 0.60 mmol, Alfa Aesar, Avocado Organics, Ward Hill, Mass.) to afford the title compound as a yellow solid. MS (ESI positive ion) m/z: 268 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.87 (s, 1H), 8.24 (s, 1H), 8.00 (d, J=9.4 Hz, 1H), 7.62 (d, J=9.4 Hz, 1H), 7.25 (t, J=1.9 Hz, 1H), 7.12-7.19 (m, 2H), 6.69-6.71 (m, 1H), 5.30 (s, 2H), 2.11 (s, 3H).

Sources & evidence

ORD record
ord-0d1f062c232e46f7889ce45c2fe8ecd6
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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