Water → HCID 178441174, compound

HRID 1696502Notes

Reaction equation

HRID 1696502 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:20])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=1.[NH2:23][C:24]1[NH:28][N:27]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:25]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[C:29]([C:26]1[CH:25]=[C:24]([NH:23][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:8]=2)=[O:20])[NH:28][N:27]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 131729653HCID 131729653, compoundHCID 178441179HCID 178441179, compound

Product 1

HCID 178441174HCID 178441174, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2,2-trichloroethyl-3-(pyridin-3-yloxy)phenylcarbamate (0.040 g, 0.11 mmol), 5-amino-3-t-butylpyrazole (0.031 g, 0.22 mmol) and i-Pr2NEt (0.029 g, 0.22 mmol) in DMF (2 mL) was stirred at 100° C. overnight. Water (20 mL) was added and the mixture was extracted with EtOAc (3×100 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 1-(3-t-butyl-1H-pyrazol-5-yl)-3-(3-(pyridin-3-yloxy)phenyl)urea (26 mg, 67% yield) of the desired product as a red-brown oil. 1H-NMR (400 MHz, CDCl3): δ 10.1 (brs, 1H), 8.40 (s, 1H), 8.35 (d, J=3.6 Hz, 1H), 8.02 (s, 1H), 7.35-7.28 (m, 4H), 6.71 (dt, J=6.4, and 2.2 Hz, 1H), 5.67 (brs, 1H), 1.32 (s, 9H), urea protons not visible; MS (EI) m/z: 352.3 (M+H+).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-f364e5924f9b45778c9450cfc593c440
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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