Azetidine → ethyl 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 2382747Notes

Reaction equation

HRID 2382747 reaction equation
CCCP(=O)=O.[CH2:7]([O:9][C:10]([C:12]1[N:13]([CH3:20])[N:14]=[CH:15][C:16]=1[C:17]([OH:19])=O)=[O:11])[CH3:8].[NH:21]1[CH2:24][CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH2:7]([O:9][C:10]([C:12]1[N:13]([CH3:20])[N:14]=[CH:15][C:16]=1[C:17]([N:21]1[CH2:24][CH2:23][CH2:22]1)=[O:19])=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 459236575-(ethoxycarbonyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 67041800ethyl 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylateYield 111.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Propylphosphonic anhydride solution (50% in ethyl acetate, 8.0 ml) was added to a cooled (0° C.) solution of 2-methyl-2H-pyrazole-3,4-dicarboxylic acid 3-ethyl ester (1.00 g, 5.0 mmol), azetidine (576 mg, 10.1 mmol), and N,N-diisopropylethylamine (2.0 g) in ethyl acetate (40 ml). The mixture was stirred for 30 min at 0° C. and overnight at r.t. The reaction mixture was taken up in ethyl acetate, washed with water, dried (Na2SO4) and evaporated. The obtained title compound (1.32 g, 99%) was used in the next step without further purification. MS (m/e)=238.3 [M+H+].

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-b097e58a6dcc4481b54be2277b417215
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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