Water → 1-[5-t-butyl-2-(3-oxo-indan-5-yl)-2H-pyrazol-3-yl]-3-(2,3-dichlorophenyl)urea

HRID 1696496Notes

Reaction equation

HRID 1696496 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][CH2:12][C:13]3=[O:16])=[CH:9][CH:8]=2)[N:5]=[C:4]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]=[C:29]=[O:30])[C:23]=1[Cl:31].O>C1COCC1>[C:17]([C:4]1[CH:3]=[C:2]([NH:1][C:29]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([Cl:21])[C:23]=2[Cl:31])=[O:30])[N:6]([C:7]2[CH:15]=[C:14]3[C:10](=[CH:9][CH:8]=2)[CH2:11][CH2:12][C:13]3=[O:16])[N:5]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 672718246-(5-Amino-3-t-butylpyrazol-1-yl)indan-1-one

Product 1

HCID 118557771-[5-t-butyl-2-(3-oxo-indan-5-yl)-2H-pyrazol-3-yl]-3-(2,3-dichlorophenyl)ureaYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the 6-(5-amino-3-t-butyl-pyrazol-1-yl)indan-1-one (1.5 g, 5.6 mmol) in THF (30 mL) was added a solution of 1,2-dichloro-3-isocyanato-benzene (1.2 g, 6.4 mmol) in THF (5.0 mL) at 0° C. under N2. The resulting mixture was stirred at RT overnight then poured into H2O. The mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, concentrated and purified via column chromatography to afford 1-[5-t-butyl-2-(3-oxo-indan-5-yl)-2H-pyrazol-3-yl]-3-(2,3-dichlorophenyl)urea as a solid (1.1 g, 43% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.22 (s, 1H), 8.68 (s, 1H), 7.94 (t, J=5.1 Hz, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.69-7.65 (m, 2H), 7.24 (d, J=4.8 Hz, 2H), 6.34 (s, 1H), 3.14-3.05 (m, 2H), 2.78-2.66 (m, 2H), 1.22 (s, 9H); MS (ESI) m/z: 457 (M+H+).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-0d60811878134555a2c4fb88dfa590ed
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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