Methylamine → HCID 58659454, compound

HRID 1993511Notes

Reaction equation

HRID 1993511 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:29][NH2:30]>>[CH3:29][NH:30][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 11742215HCID 11742215, compound

Product 1

HCID 58659454HCID 58659454, compound

Conditions

Temperature
50 °C

Procedure

1-[4-(6-Chloro-pyrimidin-4-yloxy)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea (Example 56) (42.7 mg, 0.1 mmol) is dissolved in methylamine (30% in EtOH, 1 mL) in a sealable tube and heated under Ar for 10 min at 50° C. After evaporating the solvent, the product is purified by preparative TLC (2 20×20 cm plates, acetone/CH2Cl2=3:7) to give the title compound as a white solid: M+H=404.1; 1H-NMR (400 MHz, CDCl3): 8.22 (s, 1H, pyridinyl), 7.84 (s/broad, 1H, NH), 7.62 (s, 1H, 3-CF3-phenyl), 7.52 (d, 8.0 Hz, 1H, CF3-phenyl), 7.35 (t, 8.0 Hz, 1H, 3-CF3-phenyl), 7.28 (m, 3H, CF3-phenyl/oxo-phenyl-amine), 6.97 (d, 9.5 Hz, 2H, oxo-phenyl-amine), 5.62 (d/broad, 2H, pyridinyl), 5.44 (s/broad, 1H, NH), 2.89 (s/broad, CH3—N); Rf (acetone/CH2Cl2=3:7): 0.36.

Workup

  1. customAfter evaporating the solvent
  2. customthe product is purified by preparative TLC (2 20×20 cm plates, acetone/CH2Cl2=3:7)

Sources & evidence

ORD record
ord-289728be034b4abc8cf72c70a3d12bb0
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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