N-methyl-2-pyrrolidone → HCID 18416641, compound

HRID 2188310Notes

Reaction equation

HRID 2188310 reaction equation
Cl[C:2](Cl)=[CH:3][CH:4]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[N:10]=1)=[O:8])[CH3:5].[OH-].[Na+].CN1CCC[C:31]1=[O:35]>>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([C:7]2[O:8][C:5]([CH2:31][OH:35])=[C:4]([CH2:3][CH3:2])[N:6]=2)=[N:10]1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 18416665HCID 18416665, compound

Product 1

HCID 18416641HCID 18416641, compoundYield 60%

Procedure

730 mg of 1,1-dichloro-3-[1-(2-fluorobenzyl)indazole-3-carboxamido]-but-1-ene (1.86 mmol) and 3.75 ml of NaOH, 1N (3.75 mmol) were stirred in 7.4 ml of N-methylpyrrolidone at 50° C. under argon overnight. After cooling, the mixture was poured onto ice-water and the product which had precipitated out was filtered off and dried. Finally, it was purified by column chromatography (SiO2, cyclohexane:ethyl acetate 2:1). 375 mg (60%) of 2-[1-(2-fluorobenzyl)indazol-3-yl]-5-hydroxymethyl-4-ethyl-oxazole were obtained as white crystals.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto ice-water
  3. customthe product which had precipitated out
  4. filtrationwas filtered off
  5. customdried
  6. customFinally, it was purified by column chromatography (SiO2, cyclohexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-f2679acdedf247b481dfa6326cd6293e
Source dataset
uspto-grants-2002_06
Patent number
US06410740B1

Reaction notes

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