Ammonium formate → 3-(2-Amino-5-(cyclopent-1-en-1-yl)phenyl)-1-methyl-1-propylurea

HRID 2201695Notes

Reaction equation

HRID 2201695 reaction equation
[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:20]([O-])=O)=[C:10]([NH:12][C:13](=[O:19])[N:14]([CH3:18])[CH2:15][CH2:16][CH3:17])[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[Zn]>[NH2:20][C:9]1[CH:8]=[CH:7][C:6]([C:1]2[CH2:5][CH2:4][CH2:3][CH:2]=2)=[CH:11][C:10]=1[NH:12][C:13](=[O:19])[N:14]([CH3:18])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 709817653-(5-(Cyclopent-1-en-1-yl)-2-nitrophenyl)-1-methyl-1-propylurea

Product 1

HCID 867125273-(2-Amino-5-(cyclopent-1-en-1-yl)phenyl)-1-methyl-1-propylureaYield 78.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution 3-(5-(cyclopent-1-en-1-yl)-2-nitrophenyl)-1-methyl-1-propyl urea (0.17 g, 0.56 mmol, 1.0 equiv.) in MeOH were added Zn (0.18 g, 2.80 mmol, 5.0 equiv.) and HCOONH4 (0.28 d, 4.48 mmol, 8.0 equiv.) at room temperature. The reaction was stirred for 2 h then filtered through celite. The organic layer was concentrated and the crude residue was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2) to afford 3-(2-amino-5-(cyclopent-1-en-1-yl)phenyl)-1-methyl-1-propylurea (0.12 g, 78% yield). ESI+ MS: m/z 274 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 7.61 (s, 1H), 7.08 (d, J=1.5 Hz, 1H), 7.01 (dd, J=8.0, 1.5 Hz, 1H), 6.66 (d, J=8.0 Hz, 1H), 5.94-8.90 (m, 1H), 4.77 (s, 2H), 3.24 (t, J=7.5 Hz, 2H), 2.92 (s, 3H), 2.58-2.52 (m, 2H), 2.46-2.40 (m, 2H), 1.95-1.86 (m, 2H), 1.52 (next, J=7.5 Hz, 2H), 0.86 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationthen filtered through celite
  2. concentrationThe organic layer was concentrated
  3. customthe crude residue was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b3cf9555070141c0810fc085c18e0bfd
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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