1-羟基苯并三唑(HOBT) → (S)-5-(3-[4-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-3-ethyl-thiophene-2-carbaldehyde

HRID 1685746

反应方程式

HRID 1685746 反应方程式
[CH2:1]([C:3]1[CH:4]=[C:5]([C:10]([OH:12])=O)[S:6][C:7]=1[CH:8]=[O:9])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:35][C:36]1([CH3:56])[O:40][C@@H:39]([CH2:41][O:42][C:43]2[C:52]([CH3:53])=[CH:51][C:46]([C:47]([NH:49]O)=[NH:48])=[CH:45][C:44]=2[CH2:54][CH3:55])[CH2:38][O:37]1>CN(C=O)C>[CH3:35][C:36]1([CH3:56])[O:40][C@@H:39]([CH2:41][O:42][C:43]2[C:52]([CH3:53])=[CH:51][C:46]([C:47]3[N:49]=[C:10]([C:5]4[S:6][C:7]([CH:8]=[O:9])=[C:3]([CH2:1][CH3:2])[CH:4]=4)[O:12][N:48]=3)=[CH:45][C:44]=2[CH2:54][CH3:55])[CH2:38][O:37]1

参与物

6

反应物 4

HCID 757711-羟基苯并三唑(HOBT)HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 200677334-Ethyl-5-formyl-thiophene-2-carboxylic acidHCID 178436629HCID 178436629，化合物

产物 1

HCID 86646449(S)-5-(3-[4-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-3-ethyl-thiophene-2-carbaldehyde

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

A solution of 4-ethyl-5-formyl-thiophene-2-carboxylic acid (20 mg, 0.109 mmol), HOBt (18 mg, 0.131 mmol), and EDC HCl (23 mg, 0.120 mmol) in DMF (0.75 mL) is stirred at rt for 5 min before (S)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-N-hydroxy-5-methyl-benzamidine (34 mg, 0.109 mmol) is added. The mixture is stirred at rt for 1 h, then at 85° C. for 2 days. The title compound is isolated as a colourless oil (28 mg) by separating the reaction mixture by prep. HPLC (column: Atlantis T3, 30×75 mm, 10 μm, eluting with a gradient of acetonitrile in water containing 0.5% of formic acid); LC-MS: tR=1.06 min; [M+1]+=457.19.

后处理

  1. additionis added
  2. waitat 85° C. for 2 days

来源与证据

ORD记录
ord-424cf21995cb4344bc1e3cf27af25074
来源数据集
uspto-grants-2012_04
专利号
US08148410B2

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