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

反応式

HRID 2061627 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9e5071c65577407b880d653653ca8104
出典データセット
uspto-grants-2012_10
特許番号
US08283368B2

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