Bromine → (S)-tert-Butyl(1-(4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)piperazin-1-yl)-4-methyl-1-oxopentan-2yl)carbamate

HRID 870783Notes

Reaction equation

HRID 870783 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([CH:23]=[CH:24][N:25]=3)[N:22]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[Br:31]Br>CC(O)=O>[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([C:23]([Br:31])=[CH:24][N:25]=3)[N:22]=2)[CH2:15][CH2:16]1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 86696490(S)-tert-Butyl (1-(4-(imidazo[1,2-b]pyridazin-6-yl)piperazin-1-yl)-4-methyl-1-oxopentan-2-yl)carbamate

Product 1

HCID 89805288(S)-tert-Butyl(1-(4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)piperazin-1-yl)-4-methyl-1-oxopentan-2yl)carbamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 104 mg (0.25 mmol) of (S)-tert-butyl(1-(4-(imidazo[1,2-b]pyridazin-6-yl)piperazin-1-yl)-4-methyl-1-oxopentan-2-yl)carbamate dissolved in 5 mL of AcOH was added bromine (48 mg, 0.3 mmol) and the resulting mixture was stirred at room temperature. After 0.25 hr, the reaction was done, and concentrated by rotavap and then by high vacuum pump to obtain 139 mg (100% yield) of mono-acetic acid salt of the desired product.

Workup

  1. concentrationconcentrated by rotavap

Sources & evidence

ORD record
ord-7191e60995214bea91a280d61be7c6ea
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

Loading…