Formic Acid → HCID 178505411, compound

HRID 475512Notes

Reaction equation

HRID 475512 reaction equation
C([N:8]1[C:12]2[CH2:13][CH:14]([F:16])[CH2:15][C:11]=2[C:10]([C:17]2[NH:21][N:20]=[N:19][N:18]=2)=[N:9]1)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[F:16][CH:14]1[CH2:15][C:11]2=[C:10]([C:17]3[NH:21][N:20]=[N:19][N:18]=3)[NH:9][N:8]=[C:12]2[CH2:13]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 178505391HCID 178505391, compound

Product 1

HCID 178505411HCID 178505411, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the intermediate from step B (13 mg, 0.04 mmol) in MeOH (1 mL) was added formic acid (0.1 mL) followed by palladium black (10 mg). After stirring the reaction mixture under nitrogen atmosphere for 96 hours, it was filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) to give the title compound (4.9 mg). 1H NMR (CD3OD, 500 MHz) δ 5.8 (d, J=51.9 Hz, 1H), 3.31-3.17 (m, 2H), 3.14-2.92 (m, 2H). LC-MS: 0.99 min; (M+H)=195.17.

Workup

  1. filtrationit was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by reverse phase HPLC (Gilson)

Sources & evidence

ORD record
ord-af0369c741f547c7a0db213e63681023
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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