Potassium Carbonate → 1,1-dimethylethyl 4-[4-[[methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]methyl]-2-thiazolyl]-1-piperidinecarboxylate

HRID 1966946

反応式

HRID 1966946 の反応式
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1.[CH3:21][NH:22][C@H:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:21][N:22]([CH2:2][C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1)[C@H:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amineHCID 57423790Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate2 回

生成物 1

HCID 685273541,1-dimethylethyl 4-[4-[[methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]methyl]-2-thiazolyl]-1-piperidinecarboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 1-(1,1-dimethylethyl) 4-(4-chloromethyl-2-thiazolyl)-1-piperidinecarboxylate (i.e. the product of Example 1, Step C) (0.15 g, 0.47 mmol), (1R)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (0.076 g, 0.47 mmol) and potassium carbonate (0.072 g, 0.52 mmol) in dry acetonitrile (5 mL) was heated at reflux for two days. Then the reaction mixture was filtered, concentrated under reduced pressure, diluted with dichloromethane, and washed with 1 N aqueous hydrochloric acid and water. The organic layers were dried (MgSO4) and concentrated under reduced pressure to give 0.19 g of the title compound as a tan foam.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. filtrationThen the reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with dichloromethane
  6. washwashed with 1 N aqueous hydrochloric acid and water
  7. dry with materialThe organic layers were dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cbaa9a3e9ca54f9eaccadaf70d98f468
出典データセット
uspto-grants-2013_04
特許番号
US08420673B2

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