Hydrochloric Acid → N-Cyclopropylmethyl-N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine

HRID 347862

反応式

HRID 347862 の反応式
[CH:1]1([CH2:4][N:5]([C:14]2[C:15]([CH2:23][CH3:24])=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=23)[C:6]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=O)[CH2:3][CH2:2]1.O.Cl>O1CCCC1>[CH:1]1([CH2:4][N:5]([C:14]2[C:15]([CH2:23][CH3:24])=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=23)[CH2:6][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 962Water2 回HCID 21084122N4-cyclopropylmethyl-N4-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)tetrahydro-2H-4-pyrancarboxamide

生成物 1

HCID 58801672N-Cyclopropylmethyl-N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine収率 99.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of N4-cyclopropylmethyl-N4-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)tetrahydro-2H-4-pyrancarboxamide (220 g, 672 mmol) in tetrahydrofuran (1100 mL) was stirred at an external temperature of 55° C. (hot water bath). A borane-tetrahydrofuran complex (1M solution, 1748 mL) was added dropwise to the reaction mixture, and after heating and stirring for 2 hours, the reaction mixture was cooled in an ice bath and 2N hydrochloric acid (437 mL) was added. The reaction mixture was then stirred for 1 hour at an external temperature of 50° C. (hot water bath). After the reaction terminated, a 5N aqueous sodium hydroxide solution (299 mL) was added dropwise to the reaction mixture to adjust it to pH 8, and the aqueous layer was removed. Toluene (2200 mL) was then added to the organic extract, and after washing the organic extract twice with water, it was concentrated under reduced pressure to afford 209 g of the title compound (99.2% yield).

後処理

  1. additionA borane-tetrahydrofuran complex (1M solution, 1748 mL) was added dropwise to the reaction mixture
  2. temperatureafter heating
  3. temperaturethe reaction mixture was cooled in an ice bath
  4. customAfter the reaction terminated
  5. additiona 5N aqueous sodium hydroxide solution (299 mL) was added dropwise to the reaction mixture
  6. customthe aqueous layer was removed
  7. additionToluene (2200 mL) was then added to the organic extract
  8. washafter washing the
  9. extractionorganic extract twice with water, it
  10. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-74e02cb265364bc7909c911a17050325
出典データセット
uspto-grants-2007_02
特許番号
US07176216B2

関連ノート

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