HCID 22046345, compound → HCID 22046404, compound

HRID 1821777Notes

Reaction equation

HRID 1821777 reaction equation
[N:1]([C:4]1[N:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[O:12])[CH:7]=[N:6][CH:5]=1)=[N+]=[N-].[H][H]>[Pd].[NH4+].[OH-]>[NH2:1][C:4]1[N:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[O:12])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 2

HCID 22046345HCID 22046345, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22046404HCID 22046404, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

To a stirred solution of 1-(6-azido-pyrazin-2-yl)-3-(2-methoxy-5-methyl-phenyl)-urea (8 mg, 27 μmol) 95% EtOH (2mL) at room temperature was added concentrated NH4OH (10 μL) and 10% Pd on C (25 mg). The suspension was put through a vacuum/purge cycle three times with hydrogen gas and then held under 50 psi of hydrogen pressure and shaken on a Parr Shaker. After 2 hours the vacuum/purge cycle was repeated and the reaction held under hydrogen for another 2 hours. The suspension was then filtered through GF/F filter paper with EtOH and concentrated to a yellow film (3 mg, 41%). 1H-NMR (400 MHz, CDCl3) δ 8.19 (s, 1H), 7.61 (s, 1H), 7.56 (s, 1H), 6.83 (s, 2H), 3.95 (s, 3H), 2.33 (s, 3H). LRMS (ESI, Positive) m/e 274.2 (M+1).

Workup

  1. waitthe reaction held under hydrogen for another 2 hours
  2. filtrationThe suspension was then filtered through GF/F
  3. filtrationfilter paper with EtOH
  4. concentrationconcentrated to a yellow film (3 mg, 41%)

Sources & evidence

ORD record
ord-54efbe1ca18345faab09678c9dbf8dc0
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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