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

HRID 2253396

반응식

HRID 2253396 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962Water2회HCID 21084122N4-cyclopropylmethyl-N4-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)tetrahydro-2H-4-pyrancarboxamide

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0ad16f0ce6704faa9c767bf66751712c
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323569B2

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