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

HRID 601995

反応式

HRID 601995 の反応式
[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

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 76688CyclohexanemethylamineHCID 574456983-Fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-395be85a29694ac7ba1802e257f66901
出典データセット
uspto-grants-2011_03
特許番号
US07902400B2

関連ノート

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