Water → HCID 54301864, compound

HRID 1768300Notes

Reaction equation

HRID 1768300 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16](=[O:19])[NH:17][CH3:18])[CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].CCN(CC)CC.ClC1C=CC([N:34]=[C:35]=[O:36])=CC=1C(F)(F)F.O>C(Cl)Cl>[CH3:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16](=[O:19])[NH:17][CH3:18])[CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:35]([NH2:34])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 231372464-(4-amino-3-methylphenoxy)-N-methylpyridine-2-carboxamide

Product 1

HCID 54301864HCID 54301864, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-4-(2-(N-methylcarbamoyl)(4-pyridyloxy))aniline (Method A5; 0.11 g, 0.45 mmol) in CH2Cl2 (1 mL) was treated with Et3N (0.16 mL) and 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.10 g, 0.45 mmol). The resulting brown solution was stirred at room temp. for 6 d, then was treated with water (5 mL). The aqueous layer was back-extracted with EtOAc (3×5 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to yield N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(2-methyl-4-(2-(N-methylcarbamoyl)(4-pyridyloxy))phenyl urea as a brown oil (0.11 g, 0.22 mmol): 1H NMR (DMSO-d6) δ2.27 (s, 3H), 2.77 (d, J=4.8 Hz, 3H), 7.03 (dd, J=8.5, 2.6 Hz, 1H), 7.11 (d, J=2.9 Hz, 1H), 7.15 (dd, J=5.5, 2.6, Hz, 1H), 7.38 (d, J=2.6 Hz, 1H), 7.62 (app d, J=2.6 Hz, 2H), 7.84 (d, J=8.8 Hz, 1H), 8.12 (s, 1H), 8.17 (s, 1H); 8.50 (d, J=5.5 Hz, 1H), 8.78 (q, J=5.2, 1H), 9.52 (s, 1H); HPLC ES-MS m/z 479 ((M+H)+).

Workup

  1. extractionThe aqueous layer was back-extracted with EtOAc (3×5 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7e0ca2cdf8a43d39f1b204729f320ee
Source dataset
uspto-grants-2007_06
Patent number
US07235576B1

Reaction notes

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