1-Pyrrolidineethanamine → Methyl 3-chloro-5-({[2-(1-pyrrolidinyl)ethyl]amino}carbonyl)-1H-pyrrole-2-carboxylate

HRID 1874976Notes

Reaction equation

HRID 1874976 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([C:7](Cl)=[O:8])[NH:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11].[N:14]1([CH2:19][CH2:20][NH2:21])[CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([NH:21][CH2:20][CH2:19][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:8])[NH:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 516892Sodium BicarbonateHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 68480534Methyl 3-chloro-5-({[2-(1-pyrrolidinyl)ethyl]amino}carbonyl)-1H-pyrrole-2-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.100 g, 0.387 mmol) in 4 mL of DCM was treated with [2-(1-pyrrolidinyl)ethyl]amine (0.110 g, 0.967 mmol). After 1 hour saturated NaHCO3 was added and the mixture shaken. The DCM layer was separated, dried over MgSO4 and evaporated onto silica gel. Purification was accomplished on silica with 0 to 10% MeOH in EtOAc to afford the title compound (0.080 g, 69%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.38 (t, 1H), 6.80 (d, 1H), 3.78 (s, 3H), 3.32 (q, 2H), 2.52 (t, 2H), 2.45 (br. s., 4H), 1.65 (br. s., 4H). LCMS: m/z 298.2 (M−1).

Workup

  1. customThe DCM layer was separated
  2. dry with materialdried over MgSO4
  3. customevaporated onto silica gel
  4. customPurification

Sources & evidence

ORD record
ord-d5d41936d53f49b69fc2bec33740900d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…