Water → N,3-diethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole-1-carboxamide

HRID 2113715Notes

Reaction equation

HRID 2113715 reaction equation
[N:1]([CH2:4][CH3:5])=[C:2]=[O:3].[CH2:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[N:21]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=4)[N:20]=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[NH:10][N:9]=1)[CH3:7].O.C(OCC)(=O)C>N1C=CC=CC=1>[CH2:4]([NH:1][C:2]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([C:17]3[N:21]([C:22]4[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=4)[N:20]=[CH:19][CH:18]=3)[CH:12]=2)[C:8]([CH2:6][CH3:7])=[N:9]1)=[O:3])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8022Ethyl isocyanateHCID 8857Ethyl AcetateHCID 178437987HCID 178437987, compound

Product 1

HCID 59810789N,3-diethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole-1-carboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Isocyanatoethane (0.014 mL, 0.18 mmol) was added to a solution of 3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole (50 mg, 0.14 mmol) in pyridine (2 mL) and the mixture was heated at 100° C. for 16 hours. Upon cooling, water and ethyl acetate were added and the product was washed once with 0.1 N HCl, once with water and once with brine. The combined organics were dried, the solvent was removed, and the reside was purified by column chromatography on silica gel, eluting with 20% ethyl acetate in hexanes for 5 minutes, a linear gradient to 50% ethyl acetate in hexanes over 15 minutes, and then 50% ethyl acetate for an additional 10 minutes, to afford 32 mg (54%) of N,3-diethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole-1-carboxamide. LC/MS (EI) tR 4.33 (Method C), m/z 438.2 (M++1), 1H NMR (CDCl3) δ 1.0 (t, 3H), 1.4 (t, 3H), 2.9 (t, 2H), 3.0 (s, 3H), 3.4 (m, 2H), 6.5 (s, 1H), 7.0 (d, 1H), 7.1 (s, 1H), 7.4 (d, 2H), 7.5 (m, 1H), 7.8 (s, 1H), 7.9 (d, 2H), 8.4 (s, 1H).

Workup

  1. temperatureUpon cooling
  2. washthe product was washed once with 0.1 N HCl, once with water and once with brine
  3. customThe combined organics were dried
  4. customthe solvent was removed
  5. customthe reside was purified by column chromatography on silica gel
  6. washeluting with 20% ethyl acetate in hexanes for 5 minutes
  7. wait50% ethyl acetate for an additional 10 minutes

Sources & evidence

ORD record
ord-83c642603e574cbcbf92e1a64177eb61
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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