Cyclopropylamine → Ethyl 5-(cyclopropylcarbamoyl)isoxazole-3-carboxylate

HRID 1409381Notes

Reaction equation

HRID 1409381 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([OH:13])=O)[O:8][N:7]=1)=[O:5])[CH3:2].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>C(Cl)Cl>[CH:14]1([NH:17][C:11]([C:9]2[O:8][N:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:10]=2)=[O:13])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 216484863-Ethyl 3,5-isoxazoledicarboxylate

Product 1

HCID 70980010Ethyl 5-(cyclopropylcarbamoyl)isoxazole-3-carboxylateYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared starting from 3-(ethoxycarbonyl)isoxazole-5-carboxylic acid (3.78 mmol, 0.7 g) and cyclopropyl-amine (2.91 mmol, 0.166 g) using DCM (10 ml) as the solvent. The mixture was diluted with DCM and washed with 1 M Na2CO3 and water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.284 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6) δ 0.58-0.64 (m, 2H), 0.70-0.77 (m, 2H), 1.33 (t, 3H), 2.80-2.90 (m, 1H), 4.38 (q, 2H), 7.39 (s, 1H), 9.04 (bs, 1H).

Workup

  1. customThe title compound was prepared
  2. washwashed with 1 M Na2CO3 and water
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fa272f1e318e47bf82578e78ce2619ae
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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