Tetrahydrofuran → N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide

HRID 601986

반응식

HRID 601986 반응식
C1COCC1.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]#[CH:19])[C:10](Cl)=[O:11].[CH:20]1([CH2:26][NH2:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:20]1([CH2:26][NH:27][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]#[CH:19])=[C:7]([F:6])[CH:8]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 574456843-Fluoro-4-(2-propynyloxy)benzoyl chloride

생성물 1

HCID 57445685N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide수율 64.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 10 ml of THF and 0.40 g of 3-fluoro-4-(2-propynyloxy)benzoyl chloride were added 0.45 g of cyclohexylmethylamine and 0.50 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 1 hour. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.35 g of N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 22 of the present invention) represented by the formula:

후처리

  1. customThe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7518b3286aba4f039c37a31571401569
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902400B2

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