1-Bromohexane → 5-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate

HRID 256905ノート

反応式

HRID 256905 の反応式
O.[SH-:2].[Na+].[C:4]([OH:9])(=[O:8])[C:5]([OH:7])=[O:6].Cl[C:11]1[C:15]([C:16]23[CH2:23][N:20]([CH2:21][CH2:22]2)[CH2:19][CH2:18][CH2:17]3)=[N:14][S:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CN(C=O)C.O>[C:4]([OH:9])(=[O:8])[C:5]([OH:7])=[O:6].[CH2:31]([S:2][C:11]1[C:15]([C:16]23[CH2:23][N:20]([CH2:21][CH2:22]2)[CH2:19][CH2:18][CH2:17]3)=[N:14][S:13][N:12]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

参加物

7

反応物 4

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 16211346Sodium hydrosulfide hydrateHCID 217086095-(3-Chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate

生成物 1

HCID 217086395-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate収率 49.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydrosulfide monohydrate (326 mg, 4.4 mmol) was added to a solution of 5-(3-chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate (350 mg, 1.1 mmol) in DMF (20 ml) at room temperature and the reaction mixture was stirred for 30 min. Potassium carbonate (1.24 g, 9 mmol) and 1-bromohexan (561 μl, 4 mmol) were added and the reaction mixture was stirred for 3 h. Water (50 ml) was added to the reaction mixture and the aqueous phase extracted with ether (3×200 ml). The combined ether phases were dried and evaporated to give the crude free base of the title compound (220 mg). The residue was crystallized as the oxalate salt from acetone to give the title compound. Yield 200 mg (Compound 68), m.p. 67°-69° C.

後処理

  1. stirringthe reaction mixture was stirred for 3 h
  2. extractionthe aqueous phase extracted with ether (3×200 ml)
  3. dry with materialThe combined ether phases were dried
  4. customevaporated

出典と根拠

ORDレコード
ord-d53536103116448e8dcae9823fbf6f66
出典データセット
uspto-grants-1993_11
特許番号
US05260314

反応ノート

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