Sodium Hydroxide → N-(5-(2-Amino-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl)methanesulfonamide

HRID 1162459Notes

Reaction equation

HRID 1162459 reaction equation
NC1N=C2C=CC(C3C=C(NS(C)(=O)=O)C(Cl)=NC=3)=NN2C=1C1C=CC=C(F)C=1.[Cl:30][C:31]1[N:36]=[CH:35][C:34]([C:37]2[CH:38]=[CH:39][C:40]3[N:41]([C:43]([C:50]4[CH:55]=[CH:54][N:53]=[CH:52][CH:51]=4)=[C:44]([NH:46]C(=O)C)[N:45]=3)[N:42]=2)=[CH:33][C:32]=1[NH:56][S:57]([CH3:60])(=[O:59])=[O:58].[OH-].[Na+]>>[NH2:46][C:44]1[N:45]=[C:40]2[CH:39]=[CH:38][C:37]([C:34]3[CH:33]=[C:32]([NH:56][S:57]([CH3:60])(=[O:58])=[O:59])[C:31]([Cl:30])=[N:36][CH:35]=3)=[N:42][N:41]2[C:43]=1[C:50]1[CH:51]=[CH:52][N:53]=[CH:54][CH:55]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 44125495N-(6-(6-Chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamideHCID 44125498N-(5-(2-Amino-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl)methanesulfonamide

Product 1

HCID 44125378N-(5-(2-Amino-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl)methanesulfonamideYield 72.1%

Procedure

Following the procedure described for N-(5-(2-amino-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl)methanesulfonamide (Example 23), N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (TFA salt) (Example 26) (0.040 g, 0.070 mmol) was reacted with sodium hydroxide (0.200 mL, 2.0 mmol, 10 M) at 50° C. for 28 h to afford the title compound as a yellow solid (0.0210 g, 72%). MS (ESI, positive ion) m/z: 416 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.20 (s, 3H), 6.26 (s, 2H), 7.88 (d, J=9.2 Hz, 1H), 7.95 (d, J=9.2 Hz, 1H), 8.08 (d, J=6.1 Hz, 2H), 8.57 (d, J=2.2 Hz, 1H), 8.63 (d, J=6.1 Hz, 2H), 8.89 (br s, 1H), 9.94 (br s, 1H).

Sources & evidence

ORD record
ord-50044acc6faf4c469a459f98a3913e6d
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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