HCID 68358107, compound → HCID 68295422, compound

HRID 1406011Notes

Reaction equation

HRID 1406011 reaction equation
CN(/[CH:4]=[C:5]1\[CH2:6][CH2:7][CH2:8][C:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][N:11]([CH3:19])[C:10]=2[C:20]\1=O)C.CN(C=O)C.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH2:37])=[NH:36])=[C:30]([O:38][CH3:39])[CH:29]=1>>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]2[N:37]=[C:20]3[C:10]4[N:11]([CH3:19])[N:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]=4[CH2:8][CH2:7][CH2:6][C:5]3=[CH:4][N:36]=2)=[C:30]([O:38][CH3:39])[CH:29]=1

Participants

3

Reactant 2

HCID 68358107HCID 68358107, compoundHCID 178484625HCID 178484625, compound

Product 1

HCID 68295422HCID 68295422, compoundYield 82.3%

Conditions

Temperature
120 °C

Procedure

To a suspension of ethyl (7E)-7-[(dimethylamino)methylidene]-1-methyl-8-oxo-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxylate 1.72 g (5.92 mmol) in 20 mL of DMF N-(4-Bromo-2-methoxy-phenyl)-guanidine 1.60 g (6.511 mmol) was added. The mixture was stirred at 120° C. for 4 h. The resulting mixture was cooled at room temperature and dried to dryness. The crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 4/6) to afford 2.30 g (82% yield) of the title compound as a yellow solid.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was cooled at room temperature
  3. customdried to dryness
  4. customThe crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 4/6)

Sources & evidence

ORD record
ord-38496f04049248a7b8cdf088f2eb66c5
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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