HCID 67456580, compound → HCID 49771650, compound

HRID 639607Notes

Reaction equation

HRID 639607 reaction equation
C([O:3][C:4](=O)[N:5]([C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:17]=[C:16]([NH2:24])[C:15]=1[N+:25]([O-])=O)[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)C>C(O)(=O)C.[Pd]>[NH2:24][C:16]1[C:15]2[NH:25][C:4](=[O:3])[N:5]([CH2:6][C:7]3[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[C:14]=2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:17]=1

Participants

4

Reactant 1

HCID 67456580HCID 67456580, compound

Product 1

HCID 49771650HCID 49771650, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(2-Amino-3-nitro-6-trifluoromethyl-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester (27 mg, 0.07 mmol) was stirred in glacial acetic acid (5 ml) and the solution stirred at ambient temperature, 40 psi H2, in the presence of 10% Pd/C (5.4 mg, 20% wt) for 4 h. The suspension was filtered through an Arbocel pad, washed with 2×3 ml AcOH and the filtrate concentrated in vacuo. Acetonitrile (5 ml) was added to the residue and the material triturated, the resulting solid removed by filtration and dried in vacuo to afford 10.6 mg of the title compound as a white solid. 1H NMR (d6-DMSO): δ 8.45(s, 1H), 7.57-7.55(d, 1H), 7.20-7.18(d, 1H), 7.10(s, 1H), 6.20(bs, 2H), 5.01(s, 2H), 2.40(s, 3H); LRMS (APCI) m/z 324 [MH]+

Workup

  1. filtrationThe suspension was filtered through an Arbocel pad
  2. washwashed with 2×3 ml AcOH
  3. concentrationthe filtrate concentrated in vacuo
  4. additionAcetonitrile (5 ml) was added to the residue
  5. customthe material triturated
  6. customthe resulting solid removed by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-54482b9df0d34979b68811d8b208edba
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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