对羟基苯甲醛 → N-{2-[4-Chloro-N-(4-hydroxybenzyl) cinnamylamino]ethyl}-5-isoquinolinesulfonamide

HRID 5744

反应方程式

HRID 5744 反应方程式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]=[CH:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.[OH:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:10][CH2:11][NH:12][S:13]([C:16]2[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)(=[O:14])=[O:15])[CH2:33][C:32]2[CH:35]=[CH:36][C:29]([OH:28])=[CH:30][CH:31]=2)=[CH:26][CH:27]=1

参与物

6

反应物 3

HCID 126对羟基苯甲醛HCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamideHCID 5003444氰基硼氢化钠

产物 1

HCID 53642189N-{2-[4-Chloro-N-(4-hydroxybenzyl) cinnamylamino]ethyl}-5-isoquinolinesulfonamide收率 59.3%

试剂、催化剂与溶剂 2

HCID 176醋酸催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

0.2 g of the product of Example 172 and 0.13 g of p-hydroxybenzaldehyde were dissolved in 10 ml of methanol, to the solution were added 60 mg of sodium cyanoborohydride and two drops of acetic acid, and the mixture was stirred for 2 days at a room temperature. The reaction mixture was concentrated under a reduced pressure, and after adding a saturated sodium chloride aqueous solution, extracted three times with 20 ml of ethyl acetate. The extracts were combined, washed with sodium chloride, dried over magnesium sulfate, filtered and concentrated under a reduced pressure. The resulting residue was purified on a silica gel column (silica gel 10 g, eluant: 2% methanol in chloroform), to obtain 150 mg of the title compound in a colorless amorphous form.

后处理

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. additionafter adding a saturated sodium chloride aqueous solution
  3. extractionextracted three times with 20 ml of ethyl acetate
  4. washwashed with sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified on a silica gel column (silica gel 10 g, eluant: 2% methanol in chloroform)

来源与证据

ORD记录
ord-ad93cea3c46c4c05874b445fc5c954fd
来源数据集
uspto-grants-1993_09
专利号
US05245034

关联笔记

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