Ethanol → 2-chloro-5-[3-(3-hydroxy-propylamino)-propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085636노트

반응식

HRID 2085636 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25]Cl)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C([N:30]([CH2:34][CH3:35])C(C)C)(C)C.[I-].[Na+].[CH2:38]([OH:40])C>>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][NH:30][CH2:34][CH2:35][CH2:38][OH:40])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]3)[CH2:17]1)[CH2:15]2)=[O:5]

참가 물질

5

반응물 4

HCID 702EthanolHCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 227314912-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

생성물 1

HCID 102769622-chloro-5-[3-(3-hydroxy-propylamino)-propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

반응 조건

온도
120 °C

실험 절차

To a solution of 2-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.25 g, Example 3a) and N,N-diisopropylethylamine (0.54 ml) in ethanol (5 ml) was added sodium iodide (0.08 g) and 1-propanolamine (0.24 ml). The reaction vessel was sealed and reaction mixture heated at 120° C. for 24 h. The reaction mixture was then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and sodium hydrogencarbonate solution, and the aqueous phase extracted with additional ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by NPHPLC (eluting with 0-25% ethanol in dichloromethane) to give 2-chloro-5-[3-(3-hydroxy-propylamino)-propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide as a semi-solid. This compound was converted to the hydrochloride salt by stirring with 4M HCl in dioxane and concentrated under reduced pressure to leave the title compound as a white solid (0.036 g).

후처리

  1. customThe reaction vessel was sealed
  2. customreaction mixture
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and sodium hydrogencarbonate solution
  5. extractionthe aqueous phase extracted with additional ethyl acetate
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by NPHPLC (eluting with 0-25% ethanol in dichloromethane)

출처 및 근거

ORD 기록
ord-31e9a60501f646f8863522b100d4c0cc
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720452B2

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