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

HRID 870782Notes

Reaction equation

HRID 870782 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[C:11]([O:15][C:16](=[O:31])[NH:17][C@@H:18]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:19](=[O:26])[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:14])([CH3:13])[CH3:12].C(O)(C)C>CCOC(C)=O>[C:11]([O:15][C:16](=[O:31])[NH:17][C@@H:18]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:19]([N:20]1[CH2:21][CH2:22][N:23]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:24][CH2:25]1)=[O:26])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 151444366-Fluoroimidazo[1,2-b]pyridazineHCID 598683411,1-dimethylethyl [(1S)-3-methyl-1-(1-piperazinylcarbonyl)butyl]carbamate

Product 1

HCID 86696490(S)-tert-Butyl (1-(4-(imidazo[1,2-b]pyridazin-6-yl)piperazin-1-yl)-4-methyl-1-oxopentan-2-yl)carbamateYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 305 mg (2.23 mmol) of 6-fluoroimidazo[1,2-b]pyridazine, was added 1.00 g (3.34 mmol) of (S)-tert-butyl(4-methyl-1-oxo-1-(piperazin-1-yl)pentan-2-yl)carbamate, 10 mL of isopropyl alcohol, and 0.93 mL (6.68 mmol) of TEA. This was microwaved at 150° C. for 0.5 hr. It was diluted with EtOAc, washed with brine, and the organic layer was dried over MgSO4, and then concentrated. It was purified on the ISCO with a 40 gram column eluting with 0-10% MeOH/DCM to obtain the desired product in 78% yield.

Workup

  1. customThis was microwaved at 150° C. for 0.5 hr
  2. washwashed with brine
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customIt was purified on the ISCO with a 40 gram column
  6. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-ccc26de0eb2f40a8b45e8dd4080c18ef
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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