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 2301880ノート

反応式

HRID 2301880 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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+H1 332.1165, found 332.1180.

後処理

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

出典と根拠

ORDレコード
ord-303ca484b53243e8a4ef1751bd38db64
出典データセット
uspto-grants-2002_12
特許番号
US06500840B2

反応ノート

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