4-Methoxybenzylamine → HCID 58674457, compound

HRID 1994139Notes

Reaction equation

HRID 1994139 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][NH2:40])=[CH:35][CH:34]=1>CS(C)=O.O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:17](=[O:18])[CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:40][CH2:39][C:36]4[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][CH:35]=4)[N:7]=3)[CH:10]=2)=[CH:21][C:22]=1[C:27]([F:30])([F:29])[F:28]

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 58674358HCID 58674358, compound

Product 1

HCID 58674457HCID 58674457, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 3-{3-[(2-chloropyrimidin-4-yl)oxy]phenyl}-N-[4-chloro-3-(trifluoromethyl)phenyl]propanamide (0.200 g, 0.44 mmol) in DMSO (1 mL) were added 1-(4-methoxyphenyl)methanamine (0.056 mL, 0.44 mmol) and TEA (0.061 mL, 0.44 mmol). The reaction mixture was heated at 95° C. overnight and then cooled to rt, diluted with water and extracted with EtOAc. The combined organic solutions were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give A-224. 1H NMR (400 MHz, d6 DMSO) δ: 10.35 (s, 1H), 8.11-8.15 (m, 1H), 8.05-8.11 (m, 1H), 7.75-7.81 (m, 1H), 7.62 (d, 1H), 7.30-7.39 (m, 1H), 7.09-7.26 (m, 2H), 7.04-7.07 (m, 1H), 6.67-7.00 (m, 4H), 6.05 (d, 1H), 4.25-4.43 (br m, 1H), 3.96-4.10 (br m, 1H), 3.67 (s, 3H), 2.93 (t, 2H), and 2.67 (t, 2H). LCMS, FA: Rt=1.88 min, [MH+ 557.3].

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. customto give A-224

Sources & evidence

ORD record
ord-e06281c3979e474c8a3bbcebf89f028f
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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