Tetrahydrofuran → N-cyclohexylmethyl-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide

HRID 601995

반응식

HRID 601995 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:15][CH3:16])[C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].O1CCCC1.[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(N(CC)CC)C>[CH:22]1([CH2:28][NH:29][C:5](=[O:6])[C:4]2[CH:8]=[C:9]([O:15][CH3:16])[C:10]([O:11][CH2:12][C:13]#[CH:14])=[C:2]([F:1])[CH:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 76688CyclohexanemethylamineHCID 574456983-Fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride

생성물 1

HCID 57701145N-cyclohexylmethyl-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide수율 85%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

A mixture of 200 mg of 3-fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride and 1 ml of tetrahydrofuran was added dropwise under ice cooling to a mixture of 5 ml of tetrahydrofuran, 93 mg of cyclohexylmethylamine and 100 mg of triethylamine. Then, the mixture obtained was stirred at room temperature for 0.5 hour. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 223 mg of N-cyclohexylmethyl-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 45 of the present invention) represented by the formula:

후처리

  1. customThen, the mixture obtained
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-395be85a29694ac7ba1802e257f66901
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902400B2

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