Ammonium formate → HCID 15491488, compound

HRID 2228772Notes

Reaction equation

HRID 2228772 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C@@H:10]2[CH2:15][O:14][CH2:13][CH2:12][N:11]2[CH2:16][CH:17]2[CH2:19][CH2:18]2)[C:5](=[O:20])[N:4]([CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[C:29]3[CH3:35])=[O:23])[C:3]=1[CH3:36].C([O-])=O.[NH4+]>[Pd].CO>[NH3:4].[CH:17]1([CH2:16][N:11]2[CH2:12][CH2:13][O:14][CH2:15][C@H:10]2[CH2:9][NH:8][C:6]2[C:5](=[O:20])[N:4]([CH2:21][C:22]([NH:24][CH2:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[NH:31][CH:30]=[C:29]4[CH3:35])=[O:23])[C:3]([CH3:36])=[CH:2][N:7]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69964343HCID 69964343, compound

Product 2

HCID 222AmmoniaHCID 15491488HCID 15491488, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[3-chloro-5-({[(3R)-4-(cyclopropylmethyl)morpholinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide (preparation 101) (120 mg, 0.23 mmol), ammonium formate (44 mg, 0.7 mmol) and 10% palladium on charcoal (catalytic) in methanol (5 ml) was stirred at room temperature under a nitrogen atmosphere for 64 hrs. The reaction mixture was filtered through a Whatman® filter, washing through with ethyl acetate. The combined filtrate was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:0.5) as eluant to give the title compound as a white solid, (15 mg, 14%).

Workup

  1. filtrationThe reaction mixture was filtered through a Whatman®
  2. filtrationfilter
  3. washwashing through with ethyl acetate
  4. customThe combined filtrate was evaporated under reduced pressure
  5. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-eb69e257ebbd4fe19102df263010d26d
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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