Formic Acid → HCID 117889587, compound

HRID 930535Notes

Reaction equation

HRID 930535 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][C:12]1[C:13](=[O:35])[N:14]([CH3:34])[CH:15]=[C:16]([C:18]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]=2)[CH:17]=1>>[CH2:23]([N:22]1[C:21]2[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=2[N:19]=[C:18]1[C:16]1[CH:17]=[C:12]([NH:11][CH:8]=[O:10])[C:13](=[O:35])[N:14]([CH3:34])[CH:15]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 117892031HCID 117892031, compound

Product 1

HCID 117889587HCID 117889587, compoundYield 88%

Conditions

Temperature
50 °C

Procedure

Acetic anhydride (0.050 ml; 0.518 mmol) is added to formic acid (1.000 ml; 25.974 mmol), the mixture is stirred at 50° C. for 1 h. The reaction is then cooled to RT and 3-amino-5-(1-benzyl-1H-benzoimidazol-2-yl)-1-methyl-1H-pyridin-2-one V-2 (97.000 mg; 0.294 mmol) is added in one portion. The reaction is stirred at RT for 16 h. The reaction mixture is concentrated under reduced pressure. The residue is dissolved in water/dcm (20 ml) and extracted 3 times with DCM (10 ml). The combined organic layers are dried with Na2SO4, filtered and concentrated under reduced pressure. The residue is used in the next step without further purification (yield: 88%; 93 mg; 0.259 mmol).

Workup

  1. temperatureThe reaction is then cooled to RT
  2. stirringThe reaction is stirred at RT for 16 h
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in water/dcm (20 ml)
  5. extractionextracted 3 times with DCM (10 ml)
  6. dry with materialThe combined organic layers are dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is used in the next step without further purification (yield: 88%; 93 mg; 0.259 mmol)

Sources & evidence

ORD record
ord-e68e4806f1b94febb2a9efe4c4463cf6
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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