N,N-Dimethylglycine → Ethyl 1-phenyl-1,4-dihydroimidazo[2,1-b]pyrazolo[3,4-d][1,3]thiazine-3-carboxylate

HRID 1521851Notes

Reaction equation

HRID 1521851 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][S:12][C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[C:9](Br)[N:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]=1)=[O:5])[CH3:2].CN(C)CC(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl>[C:19]1([N:8]2[C:9]3[N:17]4[CH:16]=[CH:15][N:14]=[C:13]4[S:12][CH2:11][C:10]=3[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:7]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 11430Potassium CarbonateHCID 68228885Ethyl-5-bromo-4-[(1H-imidazol-2ylthio)methyl]-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 68228168Ethyl 1-phenyl-1,4-dihydroimidazo[2,1-b]pyrazolo[3,4-d][1,3]thiazine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

Ethyl-5-bromo-4-[(1H-imidazol-2ylthio) methyl]-1-phenyl-1H-pyrazole-3-carboxylate (0.3 g, 0.74 mmol, 1 eq), Cul (14 mg, 0.074 mmol, 0.1 eq), N,N-dimethylglycine (15 mg, 0.147 mmol, 0.2 eq), K2CO3 (0.2 g, 1.47 mmol, 2 eq) are taken in DMSO (6 mL) heated at 180° C. for 0.5 h under microwave irradiation. The reaction mixture is diluted with DCM and filtered through a pad of celite. The filtrate is partitioned between DCM and water. The organic layer is washed with brine, dried over Na2SO4 and concentrated. The crude is purified by flash chromatography to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 7.67-7.59 (m, 5H), 6.93 (d, J=1.5 Hz, 1H), 6.48 (d, J=1.4 Hz, 1H), 4.40 (s, 2H), 4.34 (q, J=7.7 Hz, 2H), 1.31 (t, J=7.7 Hz, 3H). MS (ESI+): 313.2. HPLC (max plot) 97.73%; Rt 2.73 min.

Workup

  1. filtrationfiltered through a pad of celite
  2. customThe filtrate is partitioned between DCM and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude is purified by flash chromatography

Sources & evidence

ORD record
ord-3cac0e6868014ac5af9694c3e82f0f26
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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