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

HRID 1966946

반응식

HRID 1966946 반응식
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

참가 물질

5

반응물 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-carboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cbaa9a3e9ca54f9eaccadaf70d98f468
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420673B2

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