Acetic Acid → HCID 10091752, compound

HRID 2221120Notes

Reaction equation

HRID 2221120 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:11]([N+:26]([O-])=O)[CH:10]=2)=[CH:4][CH:3]=1.C(O)(=O)C>O1CCCC1>[NH2:26][C:11]1[CH:10]=[C:9]([NH:8][CH2:7][C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:14]=[CH:13][C:12]=1[NH:15][C:16](=[O:25])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 69272166HCID 69272166, compound

Product 1

HCID 10091752HCID 10091752, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred red solution of N-{4-[(5-chlorothiophen-2-ylmethyl)amino]-2-nitrophenyl}-2-(4-fluorophenyl)acetamide (320 mg, 0.762 mmol) in tetrahydrofuran (25 ml) and acetic acid (8 mL) zinc powder (particle size <10 micron, 10 g) was periodically added by portions during 30 minutes. The solution turned colorless after 5 minutes. The obtained colorless suspension was filtered via plug of SiO2 (10 g) with ethyl acetate as an eluent and the obtained solution was evaporated in vacuo. The obtained solid was dissolved in a mixture of ethyl acetate/acetone/trifluoroacetic (3 mL/3 mL/0.2 mL), treated with saturated aq. NaHCO3 (50 mL) and heptane (30 mL) and the product was separated by filtration to furnish 280 mg of a pale grey solid. Yield 94.2%. LC/MS (m/z) 390.4 ([M+H]+); RT=2.26 (UV, ELSD) 99%, 100%. 1H NMR (DMSO-d6): 3.56 (s, 2H); 4.28 (d, 2H); 4.57 (s, 2H, NH2); 5.87 (dd, 1H); 5.98 (m, 2H, NH and arom. H); 6.74 (d, 1H); 6.86 (d, 1H); 6.93 (d, 1H); 7.13 (t, 2H); 7.35 (dd, 2H); 9.10 (s, 1H).

Workup

  1. filtrationThe obtained colorless suspension was filtered via plug of SiO2 (10 g) with ethyl acetate as an eluent
  2. customthe obtained solution was evaporated in vacuo
  3. dissolutionThe obtained solid was dissolved in a mixture of ethyl acetate/acetone/trifluoroacetic (3 mL/3 mL/0.2 mL)
  4. additiontreated with saturated aq. NaHCO3 (50 mL) and heptane (30 mL)
  5. customthe product was separated by filtration

Sources & evidence

ORD record
ord-ac199c3be7644e13aba72beea56064e0
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

Loading…