N-methyl-2-pyrrolidone → HCID 69038647, compound

HRID 1276211Notes

Reaction equation

HRID 1276211 reaction equation
Cl[C:2](Cl)=[CH:3][CH:4]([NH:7][C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[N:11]=1)=[O:9])CC.[OH-:28].[Na+].CN1CC[CH2:33][C:32]1=O>>[CH2:32]([C:3]1([CH2:2][OH:28])[O:9][CH:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:11]=2)[N:7]=[CH:4]1)[CH3:33]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 18416646HCID 18416646, compound

Product 1

HCID 69038647HCID 69038647, compoundYield 52%

Procedure

1.05 g of 1,1-dichloro-3-[1-(2-fluorobenzyl)indazole-3-carboxamido]-pent-1-ene (2.58 mmol) and 5.20 ml of NaOH, 1 N (5.20 mmol) were stirred in 15 ml of N-methylpyrrolidone at 50° C. under argon for 2 days. After cooling, the mixture was poured onto ice-water and extracted several times with ethyl acetate. The organic phase was dried (sodium sulphate) and concentrated (N-methylpyrrolidone stripped off under a high vacuum). The residue was purified by column chromatography (aluminium oxide, cyclohexane/ethyl acetate 2:1). 470 mg (52%) of 5-ethyl-2-[1-(2-fluorobenzyl)-indazol-3-yl]-5-hydroxymethyl-oxazole were obtained as white crystals.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto ice-water
  3. extractionextracted several times with ethyl acetate
  4. dry with materialThe organic phase was dried (sodium sulphate)
  5. concentrationconcentrated (N-methylpyrrolidone
  6. customThe residue was purified by column chromatography (aluminium oxide, cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-55d736ec35d9460698a4b3a39c474d92
Source dataset
uspto-grants-2000_12
Patent number
US06166027

Reaction notes

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