Hydrochloric Acid → 1034025-63-2

HRID 1879129Notes

Reaction equation

HRID 1879129 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:32])=[C:14]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28]CC)=[O:27])=[CH:21][C:20]=3[CH3:31])=[O:17])[CH:15]=2)[CH:5]=[CH:6][CH:7]=1.Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:32])=[C:14]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:21][C:20]=3[CH3:31])=[O:17])[CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59760051HCID 59760051, compound

Product 1

HCID 248164341034025-63-2

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl (4-{[(5-{[(3-chlorophenyl)methyl]oxy}-2-methylphenyl)carbonyl]amino}-3-methylphenyl)acetate (174 mg, 0.39 mmol) was taken up in acetic acid (10 ml) and 2M HCl (10 ml) and heated at 90° C. for 2 hours. The reaction mixture was allowed to cool and stirring continued at room temperature overnight. The reaction mixture was extracted with ethyl acetate (50 mls), dried using a hydrophobic frit and then evaporated to dryness to give a yellow solid/gum, 155 mg. This was purified by MDAP to give the title compound as a white solid, 39 mg. MS (ES+) m/z 424 [M+H]+ (C24H2235ClNO4). 1H-NMR (400 MHz, d6-DMSO) δ 2.24 (3H, s), 2.34 (3H, s), 3.52 (2H, s), 5.17 (2H, s), 7.02-7.15 (4H, m), 7.22 (1H, d, J 8.4), 7.31 (1H, d, J 8.0), 7.39-7.44 (3H, m), 7.53 (1H, s), 9.71 (1H, s), 12.33 (1H, bs).

Workup

  1. temperatureto cool
  2. extractionThe reaction mixture was extracted with ethyl acetate (50 mls)
  3. customdried
  4. customevaporated to dryness
  5. customto give a yellow solid/gum, 155 mg
  6. customThis was purified by MDAP

Sources & evidence

ORD record
ord-945757afc34d4f2e98ea97f2a473b42f
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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