Dimethylformamide → 1-(Benzyloxycarbonyl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

HRID 337414

反応式

HRID 337414 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.CN(C=O)C.[NH2:29][C:30]1[S:31][C:32]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[C:33]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]([NH:29][C:30]2[S:31][C:32]([N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)=[C:33]([C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)=[O:19])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole2 回

生成物 1

HCID 231441071-(Benzyloxycarbonyl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-Benzyloxycarbonylpiperidine-4-carboxylic acid (5.00 g, 19.0 mmol) was dissolved in dichloromethane (80 mL), and thionyl chloride (6.93 mL, 95.0 mmol) and DMF (0.15 mL, 1.90 mmol) were added thereto, followed by stirring under heating and reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in dichloromethane (2 mL). The resulting solution was added to a solution of 2-amino-4-(2-furyl)-5-morpholinothiazole (2.01 g, 8.00 mmol) in pyridine (32 mL) obtained in Step 1 of Example 29, and then N,N-dimethylaminopyridine (97.6 mg, 0.800 mmol) was added thereto, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:3) to afford the entitled Compound 43 (4.96 g, 100%).

後処理

  1. temperatureunder heating
  2. temperaturereflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in dichloromethane (2 mL)
  5. stirringby stirring at room temperature for 1 hour
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:3)

出典と根拠

ORDレコード
ord-380679c20ae54fde87e24276a7e48ec9
出典データセット
uspto-grants-2014_11
特許番号
US08889718B2

関連ノート

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