Diisopropylethylamine → HCID 86696481, compound

HRID 870770Notes

Reaction equation

HRID 870770 reaction equation
Cl.[C@H:2]12[CH2:8][C@H:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].[Br:15][C:16]1[N:20]2[N:21]=[C:22](F)[CH:23]=[CH:24][C:19]2=[N:18][CH:17]=1.CCN(C(C)C)C(C)C>CC(O)C>[Br:15][C:16]1[N:20]2[N:21]=[C:22]([N:6]3[CH2:7][CH:2]4[CH2:8][CH:5]3[CH2:4][N:3]4[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH:23]=[CH:24][C:19]2=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazineHCID 86696479HCID 86696479, compound

Product 1

HCID 86696481HCID 86696481, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (1S,4S)-isopropyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride (0.9 g, 4.2 mmol), 3-bromo-6-fluoroimidazo[1,2-b]pyridazine (1.0 g, 4.6 mmol), and Hunig's base [7087-68-5] (3.0 mL, 17.2 mmol) in 2-propanol (21 mL) was stirred at reflux under N2 blanket for 3d then partitioned between brine and ethyl acetate. The extract was dried (MgSO4) and evaporated to obtain 1.6 g of yellow solid. LRMS (ESI) m/z 380.0/382.0 [(M+H)]+, calc'd for C16H18BrN6O2: 380.24.

Workup

  1. customthen partitioned between brine and ethyl acetate
  2. dry with materialThe extract was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-60ada039ac0f4f19a23555cfb3a9290b
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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