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

HRID 62688Notes

Reaction equation

HRID 62688 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-propylurea (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 (sext, 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-e4c70bd4cd75423a931ba6abcce855a6
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Reaction notes

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