Acetic Acid → HCID 117988125, compound

HRID 63801Notes

Reaction equation

HRID 63801 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]3=[CH:13][C:14]([C:16]([O:18]C)=[O:17])=[CH:15][N:11]3[N:10]=[C:9]([C:20]3[CH:21]=[N:22][C:23]([NH:30]C(=O)C(C)(C)C)=[CH:24][C:25]=3[C:26]([F:29])([F:28])[F:27])[N:8]=2)[CH2:3][CH2:2]1.[OH-].[K+].C(O)(=O)C>C(O)C>[NH2:30][C:23]1[N:22]=[CH:21][C:20]([C:9]2[N:8]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:12]3=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][N:11]3[N:10]=2)=[C:25]([C:26]([F:29])([F:28])[F:27])[CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 117988355HCID 117988355, compound

Product 1

HCID 117988125HCID 117988125, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 22a (300 mg, 0.59 mmol) was suspended in 10 mL of ethanol. 1.5 mL of 2 M potassium hydroxide solution was added and refluxed for 1 hour. The reaction is substantially completed. 2 mL of acetic acid was added. Most of the solvent was distilled off under reduced pressure to precipitate solids. The precipitated solids were filtered to give compound 23a. White solid (224 mg, 92.6%). m.p. 244-245° C. 1H NMR (300 MHz, DMSO-d6): δ 12.54 (s, 1H), 8.37 (s, 1H), 8.11 (s, 1H), 7.34 (s, 1H), 6.83 (s, 3H), 4.00 (t, J=4.0 Hz, 4H), 3.73 (t, J=4.0 Hz, 4H). LC-MS: 409 (M+1).

Workup

  1. temperaturerefluxed for 1 hour
  2. distillationMost of the solvent was distilled off under reduced pressure
  3. customto precipitate solids
  4. filtrationThe precipitated solids were filtered

Sources & evidence

ORD record
ord-3fb7d73258c5470bad0926e39367a8fc
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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