Triethylamine → (S)-isopropyl (1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate

HRID 870776Notes

Reaction equation

HRID 870776 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8]([N:11]3[CH2:15][CH2:14][C@H:13]([NH:16][CH3:17])[CH2:12]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].[CH2:24](N(CC)CC)C>C(Cl)Cl>[CH:22]([O:21][C:19](=[O:20])[N:16]([C@H:13]1[CH2:14][CH2:15][N:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([Br:1])=[CH:3][N:4]=3)[N:7]=2)[CH2:12]1)[CH3:17])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86696485[(S)-1-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-pyrrolidin-3-yl]-methyl-amine

Product 1

HCID 86696483(S)-isopropyl (1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamateYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(S)-1-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-pyrrolidin-3-yl]-methyl-amine (951 mg, 3.2 mmol) was taken up in DCM, and ethyl chloroformate (459 uL, 4.8 mmol) and triethylamine (895 uL, 6.4 mmol) were added. The reaction was stirred at room temperature under nitrogen for 1 hour. The reaction mixture was then washed with water then 1N HCl. The DCM layer was dried over magnesium sulfate, filtered and reduced in vacuo to give crude product (1.1 g) that was used as is in part C. LRMS (ESI) m/z 382/384 [(M+H)]+, calc'd for C15H20BrN5O2: 382.26.

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialThe DCM layer was dried over magnesium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-1fdf198ba88e49669acbd9dc98db0546
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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