Potassium Carbonate → Tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate

HRID 411524

반응식

HRID 411524 반응식
[CH:1]12[CH:8]([N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.CC1C=CC(S(O[CH2:29][CH2:30][CH2:31][NH:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:39]([C:36]1[CH:37]=[CH:38][C:33]([NH:32][CH2:31][CH2:30][CH2:29][N:3]2[CH2:4][CH:5]3[CH:8]([N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:1]([CH2:7][CH2:6]3)[CH2:2]2)=[CH:34][CH:35]=1)#[N:40]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 18541001Tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamateHCID 218676523-(4-Cyanoanilino)propyl 4-methylbenzenesulfonate

생성물 1

HCID 18540877Tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (Preparation D; 2.90 g, 12.1 mmol), 3-(4-cyanoanilino)propyl 4-methyl-benzenesulfonate (see step (ii) above; 3.98 g, 12.1 mmol), and potassium carbonate (1.67 g, 12.1 mmol) in DMF (50 mL) was heated at 90° C. under nitrogen for 4 h. The mixture was partitioned with water (50 mL) and diethyl ether (50 mL). The aqueous layer was separated and then extracted with diethyl ether (2×50 mL). The combined organic extracts were washed with saturated brine (2×30 mL), dried (Na2SO4), filtered and then concentrated in vacuo. The residue was chromatographed on silica gel, eluting with dichloromethane:methanol (98:2), to afford 2.85 g (59%) of the sub-title compound.

후처리

  1. customThe mixture was partitioned with water (50 mL) and diethyl ether (50 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with diethyl ether (2×50 mL)
  4. washThe combined organic extracts were washed with saturated brine (2×30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel
  9. washeluting with dichloromethane:methanol (98:2)

출처 및 근거

ORD 기록
ord-5c9b472e5eda40e39f44ceb0aadbadd7
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559162B2

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