Carbonic acid sodium salt (1:2) → HCID 59970488，化合物

HRID 380023

反应方程式

HRID 380023 反应方程式
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[O:32])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[O:32])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1

参与物

6

反应物 3

HCID 10340Carbonic acid sodium salt (1:2)HCID 160744-溴苯基脲HCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

产物 1

HCID 59970488HCID 59970488，化合物收率 23.6%

试剂、催化剂与溶剂 2

HCID 178418397HCID 178418397，化合物催化剂HCID 702乙醇溶剂

反应条件

温度
100 °C

实验过程

Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 33), 4-bromophenylurea (0.16 g), 2M aqueous sodium carbonate (0.25 ml) and tetrakis(triphenylphosphine)palladium (0) (0.1 g) in ethanol (3 ml). The reaction mixture was heated at 100° C. for 3 hours. After cooling, the solution was concentrated under reduced pressure. The residue was triturated with acetone and then filtered through silica gel. The filtrate was concentrated under reduced pressure and purified by flash column chromatography eluting with 10% methanol in dichloromethane give the title compound as a solid (0.046 g).

后处理

  1. customPrepared
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe residue was triturated with acetone
  5. filtrationfiltered through silica gel
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by flash column chromatography
  8. washeluting with 10% methanol in dichloromethane

来源与证据

ORD记录
ord-cd53f23750b7440aae6352185cf0202b
来源数据集
uspto-grants-2001_10
专利号
US06300352B1

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