4-Methylmorpholine → Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate

HRID 43884ノート

反応式

HRID 43884 の反応式
CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:30][CH:31]1[CH2:34][N:33]([C:35]2[S:36][C:37]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:38]([CH:40]([CH3:42])[CH3:41])[N:39]=2)[CH2:32]1.[Cl:48][C:49]1[N:50]=[C:51]([C:56](O)=[O:57])[NH:52][C:53]=1[CH2:54][CH3:55]>CC(N(C)C)=O.ClCCl.C(OCC)(=O)C>[Cl:48][C:49]1[N:50]=[C:51]([C:56]([NH:30][CH:31]2[CH2:34][N:33]([C:35]3[S:36][C:37]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:38]([CH:40]([CH3:42])[CH3:41])[N:39]=3)[CH2:32]2)=[O:57])[NH:52][C:53]=1[CH2:54][CH3:55]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67548973Ethyl 2-(3-aminoazetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 67548784Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate収率 41%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 85741463dichloromethane N,N-dimethylacetamide溶媒

実験手順

WSC hydrochloride (203 mg, 1.06 mmol), 1-hydroxybenzotriazole (48 mg, 0.35 mmol) and N-methylmorpholine (0.08 mL, 0.71 mmol) were added to a mixed solution of ethyl 2-(3-aminoazetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate obtained in Example (221b) (95 mg, 0.35 mmol) and 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (62 mg, 0.35 mmol) in DMA/dichloromethane (4 mL/2 mL), and the mixture was stirred at room temperature for 14 hours. The reaction solution was diluted with ethyl acetate, and then the mixture was washed with 10% saline and dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1) to obtain 61 mg of the title compound as a white solid (41%).

後処理

  1. washthe mixture was washed with 10% saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-a5a897ca62c5459fa5f4c48880466478
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

反応ノート

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