Dimethylformamide dimethyl acetal → HCID 178469948, compound

HRID 1487298Notes

Reaction equation

HRID 1487298 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:5]([NH:7][C:8](OC(C)(C)C)=O)[CH:6]=1.CN(C(OC)OC)C>C(Cl)Cl>[Br:1][C:2]1[N:3]=[C:4]2[C:15]([OH:22])=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=[N:7][N:5]2[CH:6]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 89995490HCID 89995490, compound

Product 1

HCID 178469948HCID 178469948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(4-bromo-1-((tert-butoxycarbonyl)amino)-1H-imidazol-2-yl)-3-oxopropanoate (1.354 g, 3.60 mmol) in DCM (23.99 ml) at room temperature was added DMF-DMA (1.446 ml, 10.80 mmol). The reaction was stirred at room temperature for 3 h. The resulting yellow suspension was concentrated under reduced pressure to give the crude cyclization product as a yellow oil. A small amount of material was triturated in CH3CN to give a pure sample of ethyl 2-bromo-8-hydroxyimidazo[1,2-b]pyridazine-7-carboxylate as a white solid. LCMS (Method B) m/z 288.0 [M+1], Br-pattern; 1H NMR (400 MHz, MeOD) δ 8.39 (s, 1H), 7.62 (s, 1H), 4.27 (q, J=7.1 Hz, 2H), 1.34 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationThe resulting yellow suspension was concentrated under reduced pressure
  2. customto give the crude cyclization product as a yellow oil
  3. customA small amount of material was triturated in CH3CN

Sources & evidence

ORD record
ord-01bdd1b966b04c98863a01eaacab949c
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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