tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate → (S)-tert-Butyl 4-(6-(6-Chloroimidazo[1,2-b]pyridazin-8-ylamino)pyridin-3-yl)-3-methylpiperazine-1-carboxylate

HRID 1024066Notes

Reaction equation

HRID 1024066 reaction equation
Cl[C:2]1C=C(NC2C=CC(N3CCN(C)CC3)=CN=2)C2N(C=CN=2)C=1.Br[C:26]1[C:27]2[N:28]([CH:33]=[CH:34][N:35]=2)[N:29]=[C:30]([Cl:32])[CH:31]=1.[NH2:36][C:37]1[N:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]2)=[CH:39][CH:38]=1>>[Cl:32][C:30]1[CH:31]=[C:26]([NH:36][C:37]2[N:42]=[CH:41][C:40]([N:43]3[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][C@@H:44]3[CH3:2])=[CH:39][CH:38]=2)[C:27]2[N:28]([CH:33]=[CH:34][N:35]=2)[N:29]=1

Participants

4

Reactant 3

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 86684119HCID 86684119, compound

Product 1

HCID 86684144(S)-tert-Butyl 4-(6-(6-Chloroimidazo[1,2-b]pyridazin-8-ylamino)pyridin-3-yl)-3-methylpiperazine-1-carboxylateYield 80%

Procedure

Following the procedure for 101b and starting with 8-bromo-6-chloroimidazo[1,2-b]pyridazine 104a (1.44 g, 6.2 mmol), and 115b (905 mg, 3.1 mmol) afforded 115c as a yellow solid (2.2 g, 80%). MS-ESI: [M+H]+ 444.2

Sources & evidence

ORD record
ord-d4399297d51b4e369b15fc47ff22c76a
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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