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Hydrochloric Acid → HCID 86648485、化合物

HRID 1424941
ノート
印刷プレビュー

反応式

HRID 1424941 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18](OC(C)(C)C)=O)[CH2:14][C@H:13]2[O:25][CH3:26])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.C(OCC)(=O)C.C(N(C(C)C)CC)(C)C.ClC1[S:45][C:46]([CH3:54])=[C:47]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[N:48]=1.Cl>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:45][C:46]([CH3:54])=[C:47]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[N:48]=3)[CH2:14][C@H:13]2[O:25][CH3:26])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 53302340Ethyl 2-chloro-5-methyl-1,3-thiazole-4-carboxylateHCID 86648452tert-Butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

生成物 1

HCID 86648485
HCID 86648485、化合物
収率 16%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

tert-Butyl cis(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1g) (80 mg, 0.21 mmol) was dissolved in methanol (1 mL). A 4 N hydrochloric acid/ethyl acetate solution (3 mL) was added, and the mixture was stirred at room temperature for one hour. Following concentration under reduced pressure, the residue was dissolved in DMF (2 mL). Diisopropylethylamine (0.16 mL, 0.92 mmol) and ethyl 2-chloro-5-methyl-1,3-thiazole-4-carboxylate obtained in Example (38a) (70 mg, 0.34 mmol) were added, and the mixture was stirred using a microwave reactor at 160° C. for three hours. Dilute hydrochloric acid was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, ethyl acetate) to obtain 15.3 mg of the title compound as a pale yellow solid (16%).

後処理

  1. concentrationconcentration under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (2 mL)
  3. stirringthe mixture was stirred
  4. customat 160° C.
  5. customfor three hours
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate solution and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentration under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, ethyl acetate)

出典と根拠

ORDレコード
ord-8586d4ea1de34ce2ab46c90d6d5952ce
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927588B2

反応ノート

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