Ammonium formate → N-cyclopropyl-3-fluoro-5-[3-[[1-(2-hydroxyphenyl)-1-methylethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide

HRID 337087Notes

Reaction equation

HRID 337087 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:23][C:24]([CH3:40])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32]CC2C=CC=CC=2)[CH3:25])[C:5](=[O:22])[N:6]([C:8]2[CH:9]=[C:10]([CH:17]=[C:18]([F:21])[C:19]=2[CH3:20])[C:11]([NH:13][CH:14]2[CH2:16][CH2:15]2)=[O:12])[CH:7]=1.C([O-])=O.[NH4+]>[Pd]>[CH:14]1([NH:13][C:11](=[O:12])[C:10]2[CH:9]=[C:8]([N:6]3[CH:7]=[CH:2][N:3]=[C:4]([NH:23][C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[OH:32])([CH3:25])[CH3:40])[C:5]3=[O:22])[C:19]([CH3:20])=[C:18]([F:21])[CH:17]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 666887063-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide

Product 1

HCID 66689080N-cyclopropyl-3-fluoro-5-[3-[[1-(2-hydroxyphenyl)-1-methylethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
75 °C

Procedure

To 3-[5-bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide (Example 252i, 9.84 g) was added 10% Pd/C (1.729 g) and ammonium formate (14.35 g). The reaction was heated at 75° C. for 2 h then filtered through celite and washed with ethanol. The filtrate was collected and the volatiles removed in vacuo and the resulting crude product was taken up in dichloromethane and washed with water. The organic layer dried (MgSO4) and the solvent removed in vacuo and the residue triturated with diethyl ether to afford subtitle product (7.08 g).

Workup

  1. filtrationthen filtered through celite
  2. washwashed with ethanol
  3. customThe filtrate was collected
  4. customthe volatiles removed in vacuo
  5. washwashed with water
  6. dry with materialThe organic layer dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-50f45e0144c248118d725e4381cf7918
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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