Benzene, 1-isocyanato-4-nitro- → 1-(4-nitro-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-urea

HRID 1790111Notes

Reaction equation

HRID 1790111 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C1COCC1>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:28]([NH:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:9]=[CH:10]3)=[O:29])=[CH:25][CH:26]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 66012Benzene, 1-isocyanato-4-nitro-HCID 113107771-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-5-ylamine

Product 1

HCID 220366191-(4-nitro-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-ureaYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (2.0 g, 8.7 mmol) and 4-nitrophenyl isocyanate (1.5 g, 8.8 mmol) in 150 mL of THF was heated to reflux for 2 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in 100 mL of ethyl acetate and tritutrated to provide a precipitate which was collected filtration to provide the title compound (3.1 g, 91%). 1H NMR (300 MHz, DMSO-d6) ppm 1.64 (m, 4H), 2.45 (m, 4H), 2.86 (d, J=6.44, 2H), 4.48 (d, J=6.44, 2H), 7.37 (m, 1H), 7.63 (m, 1H), 7.70 (m, 2H), 7.90 (m, 1H), 7.99 (s, 1H), 8.19 (m, 2H), 8.89 (s, 1H), 9.43 (s, 1H); MS (DCI/NH3) m/z 395 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customto provide a precipitate which
  5. customwas collected
  6. filtrationfiltration

Sources & evidence

ORD record
ord-b726e01817984974ba9b23a2f9838f16
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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