Water → Ethyl 1-ethyl-5-(2-phenylimidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate

HRID 1958332Notes

Reaction equation

HRID 1958332 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][N:10]3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:25]([C:27]1[N:31]([CH2:32][CH3:33])[N:30]=[CH:29][C:28]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:26].O>ClCCl>[CH2:32]([N:31]1[C:27]([C:25](=[O:26])[NH:15][C:13]2[CH:12]=[CH:11][N:10]3[CH:16]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]3[N:14]=2)=[C:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:29]=[N:30]1)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amineHCID 86657899Ethyl 5-(chlorocarbonyl)-1-ethyl-1H-pyrazole-4-carboxylate

Product 1

HCID 53467806Ethyl 1-ethyl-5-(2-phenylimidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Phenylimidazo[1,2-a]pyrimidin-7-amine (example 1, step 1, 648 mg, 3.08 mmol) and triethylamine (519 mg, 715 μA, 5.13 mmol) were combined with dichloromethane (15 ml) to give a light brown solution. Ethyl 5-(chlorocarbonyl)-1-ethyl-1H-pyrazole-4-carboxylate (1.6 g, 2.57 mmol) was diluted in dichloromethan and was added dropwise at 0° C. The reaction was stirred overnight. The reaction mixture was poured into 20 mL water and extracted with dichloromethan (2×50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 50% to 100% EtOAc in heptane). The obtained product contained the imide (2 acid chlorides added to amine) as an impurity, but was used in the next step (where the title compound and the impurity give the same product). The title compound was obtained as a light brown solid (510 mg, 49.1%).

Workup

  1. customto give a light brown solution
  2. additionwas added dropwise at 0° C
  3. extractionextracted with dichloromethan (2×50 mL)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 50 g, 50% to 100% EtOAc in heptane)
  7. customthe impurity give the same product)

Sources & evidence

ORD record
ord-bf012d794a48481aa81943e2c4952784
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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