Carbon Dioxide → 4-((2-Fluoroethyl)(methyl)carbamoyl)-1-methyl-1H-pyrazole-5-carboxylic acid

HRID 1802171

反応式

HRID 1802171 の反応式
[F:1][CH2:2][CH2:3][N:4]([CH3:13])[C:5]([C:7]1[CH:8]=[N:9][N:10]([CH3:12])[CH:11]=1)=[O:6].CN(C)CCN(C)CCN(C)C.[Li]C(C)(C)C.[C:31](=[O:33])=[O:32]>C1COCC1>[F:1][CH2:2][CH2:3][N:4]([CH3:13])[C:5]([C:7]1[CH:8]=[N:9][N:10]([CH3:12])[C:11]=1[C:31]([OH:33])=[O:32])=[O:6]

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 18196PentamethyldiethylenetriamineHCID 58446960HCID 58446960、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 584468624-((2-Fluoroethyl)(methyl)carbamoyl)-1-methyl-1H-pyrazole-5-carboxylic acid収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-100 °C

実験手順

In a 50 mL three-necked flask, N-(2-fluoroethyl)-N,1-dimethyl-1H-pyrazole-4-carboxamide (500 mg, 2.7 mmol) was combined with THF (10.0 ml) to give a colorless solution. 1,1,4,7,7-Pentamethyldiethylenetriamine (621 μl, 2.97 mmol) was added, and, after cooling down to −100° C., tBuLi (1.6 M in pentane, 2.53 ml, 4.05 mmol) was added dropwise. After stirring 30 min an excess of dry ice was carefully added. After 5 min, the cooling bath was removed and the mixture was allowed to warm up to RT. H2O was added and un-reacted starting material was removed by extraction with CH2Cl2. The aqueous layer was then acidified using 1 N HCl solution, and the acid was extracted using CH2Cl2. After drying over Na2SO4, filtration and concentration in vacuum, the viscous oil was dried in HV to yield 307 mg (50%) of product as a light brown viscous oil. MS: m/z=230.2 [M+H]+.

後処理

  1. customto give a colorless solution
  2. additionwas carefully added
  3. customthe cooling bath was removed
  4. temperatureto warm up to RT
  5. additionH2O was added
  6. customun-reacted
  7. customwas removed by extraction with CH2Cl2
  8. extractionthe acid was extracted
  9. dry with materialAfter drying over Na2SO4, filtration and concentration in vacuum
  10. customthe viscous oil was dried in HV

出典と根拠

ORDレコード
ord-5a42e9a144ec4a7cae3dc97de1d026c4
出典データセット
uspto-grants-2013_01
特許番号
US08349824B2

関連ノート

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