Cyclopropylamine → Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylate

HRID 1874970Notes

Reaction equation

HRID 1874970 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[Cl:5][C:6]1[CH:10]=[C:9]([C:11]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 68484245Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylateYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cycloproplyamine (0.166 g, 2.90 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.150 g, 0.580 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. The solvent was evaporated and purification was accomplished by silica gel column chromatography (30-100% EtOAc/hexanes) to afford the title compound (0.099 g, 70%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.81 (br. s., 1H), 7.71 (br. s., 1H), 6.78 (s, 1H), 3.84 (s, 3H), 2.79-2.92 (m, 1H), 0.73 (d, 2H), 0.57 (d, 2 H) LCMS: m/z 243.1 (M+1).

Workup

  1. customThe solvent was evaporated
  2. custompurification

Sources & evidence

ORD record
ord-ea2b2e9b11064fb083e91dc628a5f7d5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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