Water → HCID 58416747, compound

HRID 1916820Notes

Reaction equation

HRID 1916820 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH2:25][CH2:26]I)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[N+:41]([C:44]1[N:45]=[CH:46][NH:47][CH:48]=1)([O-:43])=[O:42].O>CN(C=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH2:25][CH2:26][N:47]3[CH:48]=[C:44]([N+:41]([O-:43])=[O:42])[N:45]=[CH:46]3)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 183385211-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-(4-(2-iodoethoxy)naphthalen-1-yl)ureaHCID 178526856HCID 178526856, compound

Product 1

HCID 58416747HCID 58416747, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-(4-(2-iodoethoxy)naphthalen-1-yl)urea (J. Med. Chem., 2003, 46, 4676-4686) (400 mg, 0.704 mmol), potassium carbonate (292 mg, 2.111 mmol) and 4-nitroimidazole (88 mg, 0.774 mmol) in DMF (2.0 mL) was placed in a pre-heated oil bath at 50° C. and stirred for 16 hr. The mixture was cooled to RT, poured into water (5.0 mL) and extracted with EtOAc (5.0 mL×2). The combined organic layers were dried, filtered and evaporated and the resulting residue was subjected to column chromatography (40 g), eluting with EtOAc to give 1-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-(4-(2-(4-nitro-1H-imidazol-1-yl)ethoxy)naphthalen-1-yl)urea (35) as a brown solid (276 mg, 60%): m/z 554 (M+H)+ (ES+).

Workup

  1. customwas placed in a pre-heated oil bath at 50° C.
  2. extractionextracted with EtOAc (5.0 mL×2)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. customevaporated
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-5e3edd2f61cc4bb0be9aedbc8b708d8f
Source dataset
uspto-grants-2013_12
Patent number
US08618140B2

Reaction notes

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