3-Pentanamine → Methyl [4-bromo-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate

HRID 2373712Notes

Reaction equation

HRID 2373712 reaction equation
[Br:1][C:2]1[C:3]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[S:5][CH:6]=1.[NH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:13])=[CH:14][CH:15]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 692003654-(4-Bromo-3-methoxycarbonylmethyl-thiophen-2-yl)-benzoic acid

Product 1

HCID 86607182Methyl [4-bromo-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetateYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Bromo-3-methoxycarbonylmethyl-thiophen-2-yl)-benzoic acid (0.303 g, 0.85 mmol) was dissolved in DMF (2 mL) and carbonyldiimidizole (0.172 g, 1.06 mmol) was added. The solution was stirred at RT for thirty minutes and 3-aminopentane (0.222 g, 2.55 mmol) was added. Stirring was continued for 3 h and the solvent was removed. The mixture was partitioned between EtOAc and H2O. The EtOAc was dried (MgSO4) and the solvent was removed to yield methyl [4-bromo-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate (0.248 g) as a white solid. mp 97-98° C.; 1H NMR (500 MHz, DMSO-d6) δ: 0.87 (t, 6H, J=7.3 Hz), 1.49 (m, 2H), 1.54 (m, 2H), 3.65 (s, 3H), 3.71 (s, 2H), 3.80 (m, 1H), 7.51 (d, 1H, J=8.5 Hz), 7.85 (s, 1H), 7.95 (d, 2H, J=8.5 Hz), 8.12 (d, 1H, J=8.7 Hz). MS (ES) m/z 424.0 ([M+H]+). MS (ES) m/z 456.0 ([M+CH3OH+H]+). MS (ES) m/z 847.0 ([2M+H]+). Anal. Calcd for C19H22BrNO3S: C, 53.78; H, 5.23; N, 3.30. Found: C, 53.65; H, 4.77; N, 3.52.

Workup

  1. additioncarbonyldiimidizole (0.172 g, 1.06 mmol) was added
  2. stirringStirring
  3. customthe solvent was removed
  4. customThe mixture was partitioned between EtOAc and H2O
  5. dry with materialThe EtOAc was dried (MgSO4)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-fffb663a12fb4cdaada0ba85a386ab82
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

Loading…