Formic Acid → HCID 86678996, compound

HRID 2203361Notes

Reaction equation

HRID 2203361 reaction equation
[CH:1](O)=[O:2].[NH2:4][C:5]1[C:6]2[C:31]([CH3:36])([C:32]([NH:34][NH2:35])=[O:33])[C:30](=[O:37])[NH:29][C:7]=2[N:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[N:12]=2)[N:10]=1>C(#N)C>[NH2:4][C:5]1[C:6]2[C:31]([CH3:36])([C:32]([NH:34][NH:35][CH:1]=[O:2])=[O:33])[C:30](=[O:37])[NH:29][C:7]=2[N:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][C:22]([F:28])([F:27])[C:23]([F:25])([F:24])[F:26])[N:12]=2)[N:10]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 86678995HCID 86678995, compound

Product 1

HCID 86678996HCID 86678996, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Formic acid (3 mL, 78 mmol) was added to an acetonitrile solution (3 mL) of the intermediate from Step A (200 mg, 0.371 mmol). The reaction mixture was heated at 80° C. for 1.5 hours in a screw cap vial. The mixture was cooled, concentrated in vacuo and the residue diluted with EtOAc. The solution was then washed with saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a pale yellow solid which was used in the next step without further purification. m/z=513.97 (M+H).

Workup

  1. customcap vial
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. additionthe residue diluted with EtOAc
  5. washThe solution was then washed with saturated aqueous sodium bicarbonate, water and brine
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e9fb91e7c7724032a885ff1ffafde739
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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