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

HRID 1425342ノート

反応式

HRID 1425342 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:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][N:39]=2)[CH2:32]1.[Cl:45][C:46]1[N:47]=[C:48]([C:53](O)=[O:54])[NH:49][C:50]=1[CH2:51][CH3:52]>CC(N(C)C)=O.ClCCl.C(OCC)(=O)C>[Cl:45][C:46]1[N:47]=[C:48]([C:53]([NH:30][CH:31]2[CH2:34][N:33]([C:35]3[S:36][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][N:39]=3)[CH2:32]2)=[O:54])[NH:49][C:50]=1[CH2:51][CH3:52]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67548752Ethyl 2-(3-aminoazetidin-1-yl)-1,3-thiazole-5-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

生成物 1

HCID 67548970Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-thiazole-5-carboxylate収率 64%

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 (62 mg, 0.32 mmol), 1-hydroxybenzotriazole (36 mg, 0.27 mmol) and N-methylmorpholine (0.06 mL, 0.54 mmol) were added to a mixed solution of ethyl 2-(3-aminoazetidin-1-yl)-1,3-thiazole-5-carboxylate obtained in Example (217b) (61 mg, 0.27 mmol) and 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (47 mg, 0.27 mmol) in DMA/dichloromethane (2 mL/2 mL), and the mixture was stirred at room temperature for 19 hours. The reaction solution was diluted with ethyl acetate, and then the mixture was washed with brine 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: dichloromethane/methanol=20/1) to obtain 66 mg of the title compound as a white solid (64%).

後処理

  1. washthe mixture was washed with brine
  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: dichloromethane/methanol=20/1)

出典と根拠

ORDレコード
ord-58278fcc1a9a4447a8f32cf4a0fc569a
出典データセット
uspto-grants-2015_01
特許番号
US08927588B2

反応ノート

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