Acetic Acid → HCID 11301616, compound

HRID 2354230Notes

Reaction equation

HRID 2354230 reaction equation
[CH2:1](OC(OCC)OCC)C.[NH2:11][C:12]1[CH:33]=[CH:32][CH:31]=[CH:30][C:13]=1[C:14]([NH:16][C:17]1[CH:18]=[C:19]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:20]([NH:22][CH:23]1[CH2:25][CH2:24]1)=[O:21])=[O:15].C(O)(=O)C>C(O)C>[CH:23]1([NH:22][C:20](=[O:21])[C:19]2[CH:26]=[CH:27][C:28]([CH3:29])=[C:17]([N:16]3[C:14](=[O:15])[C:13]4[C:12](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:11]=[CH:1]3)[CH:18]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 66918852HCID 66918852, compound

Product 1

HCID 11301616HCID 11301616, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Triethylorthoformate (0.15 ml) was added to a stirred mixture of 3-[(2-aminobenzoyl)amino]-N-cyclopropyl-4-methylbenzamide (0.093 g) and glacial acetic acid (0.017 ml) in ethanol (10 ml). The mixture was heated to 80° C. and stirred for 16 hours. The reaction mixture was evaporated, dissolved in ethyl acetate (50 ml) and washed with a saturated NaHCO3 solution (100 ml). The organic phase was dried over magnesium sulphate, filtered then concentrated in vacuo onto silica gel (0.1 g). The residue was purified by column chromatography (isolute silica 20 g column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using a gradient of 10% iso-propanol/iso-hexane through to 50% iso-propanol/iso-hexane to give the title compound as a white solid (0.062 g); NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.68 (m, 2H), 2.14 (s, 3H), 2.84 (m, 1H), 7.52 (d, 1H), 7.62 (t, 1H), 7.78 (d, 1H), 7.84 (d, 1H), 7.89 (m, 2H), 8.21 (m, 1H), 8.30 (s, 1H), 8.41 (d, 1H); Mass Spectrum: M+H+ 320.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in ethyl acetate (50 ml)
  3. washwashed with a saturated NaHCO3 solution (100 ml)
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo onto silica gel (0.1 g)
  7. customThe residue was purified by column chromatography (isolute silica 20 g column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)

Sources & evidence

ORD record
ord-9187b05efaa2430fabc802a50e9b1a01
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

Loading…