Sodium Iodide → (S)-2-(4-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)butyl)isoindoline-1,3-dione

HRID 2061627

반응식

HRID 2061627 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[CH3:25][CH2:26][CH2:27][NH:28][C@@H:29]1[CH2:38][C:33]2[S:34][C:35]([NH2:37])=[N:36][C:32]=2[CH2:31][CH2:30]1>C(#N)C>[NH2:37][C:35]1[S:34][C:33]2[CH2:38][C@@H:29]([N:28]([CH2:27][CH2:26][CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]4[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:7]3=[O:16])[CH2:30][CH2:31][C:32]=2[N:36]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 119570Pramipexole

생성물 1

HCID 58369715(S)-2-(4-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)butyl)isoindoline-1,3-dione수율 90.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-(4-bromobutyl)-phthalimide (2.25 g, 7.98 mmol), cesium carbonate (2.6 g, 7.98 mmol), and sodium iodide (1.80 g, 12 mmol) were added to a solution of pramipexole 1 (1.53 g, 7.25 mmol) in acetonitrile (50 mL). After refluxing for 3 hours, the mixture was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, and dried over anhydrous Na2SO4. Flash column chromatography (MeOH/EtOAc, 5:95) gave 13 as a colorless oil (2.7 g, 90.4%). 1H NMR (CDCl3, 300 MHz) δ 7.88-8.00 (m, 2H), 7.78-7.60 (m, 2H), 4.90 (s, 2H), 3.70 (t, J=7.2 Hz, 2H), 3.10-2.95 (m, 1H), 2.78-2.30 (m, 8H), 2.05-1.90 (m, 1H), 1.77-1.60 (m, 3H), 1.56-1.40 (m, 4H), 0.87 (t, J=7.2 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ168.89, 165.83, 145.53, 134.28, 132.53, 123.58, 117.96, 57.59, 52.97, 50.41, 38.34, 27.01, 26.81, 26.71, 26.05, 25.33, 22.64, 12.24.

후처리

  1. temperatureAfter refluxing for 3 hours
  2. customthe mixture was evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4

출처 및 근거

ORD 기록
ord-9e5071c65577407b880d653653ca8104
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283368B2

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