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

HRID 726572노트

반응식

HRID 726572 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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-bromohexane (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.

후처리

  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

출처 및 근거

ORD 기록
ord-14f995fb601c4def986e6e18d2af6f08
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710151

반응 노트

불러오는 중…