1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (+/-)-4-(4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877816Notes

Reaction equation

HRID 877816 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9]([NH:10][CH:11]3[C:15]([CH3:17])([CH3:16])[CH2:14][N:13]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12]3)=[C:8]([C:22]([NH2:24])=[O:23])[CH:7]=[N:6][N:5]2[CH:25]=1.[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1>>[CH3:16][C:15]1([CH3:17])[CH2:14][N:13]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH:11]1[NH:10][C:9]1[C:4]2[N:5]([CH:25]=[C:2]([C:30]3[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=3)[CH:3]=2)[N:6]=[CH:7][C:8]=1[C:22]([NH2:24])=[O:23]

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 68350406(+/-)-6-Bromo-4-((4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68350506(+/-)-4-(4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

Procedure

The title compound was prepared according to the procedure described for Example 297 by Suzuki coupling with (+/−)-6-bromo-4-(4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (from Step 1 of Example 297) with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Sources & evidence

ORD record
ord-2330641d30c843d989774ba220b2aea0
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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