Triethylamine → HCID 70660125, compound

HRID 877280Notes

Reaction equation

HRID 877280 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][C:20]=3[NH2:25])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1.C(N(CC)CC)C>C1COCC1.[Pd]>[F:26][C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=1[C:8]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[NH2:25])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 52919131HCID 52919131, compound

Product 1

HCID 70660125HCID 70660125, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

353 mg N*4*-[2-(5-Chloro-2-fluoro-phenyl)-quinolin-4-yl]-pyridine-3,4-diamine (cf. Example 7) dissolved in 60 ml THF and 330 mg triethylamine were hydrogenated over 1.8 g Pd—C (52% water) over night, at normal pressure and ambient room temperature to give after filtration, evaporation and subsequent digeration with ether 238 mg yellow powder product with correct mass M+H+331 and >90% HPLC purity with a Rt˜1.23 min in LC-MS system 1. TLC on silica in CH2Cl2/MeOH 1:1 showed one product at Rf˜0.21.

Workup

  1. customto give
  2. filtrationafter filtration, evaporation and subsequent digeration with ether 238 mg yellow powder product with correct mass M+H+331 and >90% HPLC purity with a Rt˜1.23 min in LC-MS system 1

Sources & evidence

ORD record
ord-37402d33f7f6428aae26e7388dbbca30
Source dataset
uspto-grants-2015_03
Patent number
US08987301B2

Reaction notes

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