HCID 136242908, compound → HCID 136242912, compound

HRID 1775210Notes

Reaction equation

HRID 1775210 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][CH:10]=[CH:11][C:12]3[NH:13][C:14]4[CH2:15][N:16](C(OCC5C=CC=CC=5)=O)[CH2:17][C:5]([C:6]=4[C:7]=32)=[N:4][NH:3]1.[H][H]>CO.[Pd]>[CH2:17]1[NH:16][CH2:15][C:14]2[NH:13][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:2](=[O:1])[NH:3][N:4]=[C:5]1[C:6]=2[C:7]=34

Participants

5

Reactant 2

HCID 136242908HCID 136242908, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136242912HCID 136242912, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Compound 20 (34 mg, 0.1 mmol) and palladium (10%) on carbon (10 mg) in 10 mL of methanol was stirred at RT under a balloon of hydrogen for 5 h. The mixture was then filtered through a pad of celite. The catalyst cake was washed with methanol. The filtrate was concentrated. The resulting residue was purified by HPLC to give the target product as formic acid salt (white solid) (13 mg, 50%). 1H NMR (DMSO-d6) δ 11.7 (s, 1H), 9.86 (s, 1H), 7.40-7.45 (m, 2H), 7.09 (t, 1H, J=8.0 Hz), 3.94 (s, 2H), 3.41 (s, 2H). MS (ESI) m/e [M+1]+ 227.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. washThe catalyst cake was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. customThe resulting residue was purified by HPLC
  5. customto give the target product as formic acid salt (white solid) (13 mg, 50%)

Sources & evidence

ORD record
ord-c24dd739ddb74fed9996ae677f0dd2c9
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

Loading…