Borane,N-dimethylmethanamine (1:1) → 2-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamide

HRID 1882961노트

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HRID 1882961 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[N:15][C:16]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[B-][N+](C)(C)C>C(O)(=O)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

참가 물질

4

반응물 2

HCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 219061692-(1-Boc-piperidin-4-ylmethylidene)amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamide

생성물 1

HCID 219066432-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamide수율 97%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
70 °C

실험 절차

A solution containing 2-(1-Boc-piperidin-4-yl-methylidene)amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamide from above (6.0 g, 13 mmol) and borane trimethylamine complex (2.9 g, 39 mmol) in glacial acetic acid (100 mL) was heated at 70° C. for 24 h. The solution was allowed to cool to room temperature; then the solvent was removed in vacuo, and the residue was partitioned between dichloromethane (200 mL) and water (100 mL). The biphasic mixture was treated with 2 N NaOH until neutral; then the organic layer was separated and the aqueous layer was washed again with dichloromethane (100 mL). The combined organic layers were washed with brine (100 mL), dried with MgSO4, and filtered. The filtrate was concentrated in vacuo to give 5.85 g (97%) of the title compound as an orange foam which was used directly in the next step without further purification.

후처리

  1. temperatureto cool to room temperature
  2. customthen the solvent was removed in vacuo
  3. customthe residue was partitioned between dichloromethane (200 mL) and water (100 mL)
  4. additionThe biphasic mixture was treated with 2 N NaOH until neutral
  5. customthen the organic layer was separated
  6. washthe aqueous layer was washed again with dichloromethane (100 mL)
  7. washThe combined organic layers were washed with brine (100 mL)
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5a35aae837ff40cc9714cb11a61c8f5c
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759414B2

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