p-Toluenesulfonic acid monohydrate → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-(3-chlorophenyl)-1,3-oxazole-2-carboxamide 4-methylbenzenesulfonate

HRID 1359651노트

반응식

HRID 1359651 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([C:13]([O:15]CC)=O)=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:18][C@@H:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>CCO>[CH3:38][C:28]1[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:32][CH:33]=1.[N:21]12[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22]1)[C@@H:19]([NH:18][C:13]([C:11]1[O:12][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[CH:9][N:10]=1)=[O:15])[CH2:20]2

참가 물질

5

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 719215(3R)-1-Azabicyclo(2.2.2)octan-3-amineHCID 22350710Ethyl 5-(3-chlorophenyl)oxazole-2-carboxylate

생성물 1

HCID 86584883N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-(3-chlorophenyl)-1,3-oxazole-2-carboxamide 4-methylbenzenesulfonate수율 70.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of the product from Step 79c (0.419 g, 1.66 mmol, 1.0 eq), (R)-(+)-3-aminoquinuclidine (0.221 g, 1.75 mmol, 1.05 eq) and EtOH (4.0 mL) is heated under reflux. After 64 h, the mixture is cooled and the contents are filtered through glass wool into p-toluenesulfonic acid monohydrate (0.315 g, 1.65 mmol, 1.0 eq). The resulting solid is filtered and dried in vacuo to afford the title compound (0.59 g, 65%). HRMS (FAB) calculated for C17H18ClN3O2+Hl 332.1165, found 332.1180.

후처리

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturethe mixture is cooled
  4. filtrationThe resulting solid is filtered
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-2189893c9c134ec6af186065e4b1e58e
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599916B2

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