Hexane → Benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-(3-ethoxy-benzyl)-amine

HRID 457366

反応式

HRID 457366 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)[CH3:2].[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][NH:22][CH2:23][C:24]3[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[C:28]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:27]=[N:26][C:25]=3[Cl:40])=[CH:20][C:15]=2[O:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCCCCC>CC(O)=O.CCOC(C)=O>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][N:22]([CH2:23][C:24]3[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[C:28]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:27]=[N:26][C:25]=3[Cl:40])[CH2:7][C:6]3[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)=[CH:20][C:15]=2[O:14][CH2:13]1

参加物

7

反応物 4

HCID 8058HexaneHCID 899083-EthoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18438149Benzo[1,3]dioxol-5-ylmethyl (5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine

生成物 1

HCID 18437597Benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-(3-ethoxy-benzyl)-amine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Ethoxybenzaldehyde (0.062 ml, 0.44 mmol) is added to a solution of benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine) (0.045 g, 0.1 mmol) in CH2ClCH2Cl (5 mL) and HOAc (0.5 mL). The mixture is stirred at room temperature for 45 minutes, NaBH(OAc)3 (0.140 g, 0.66 mmol) is then added and the mixture is stirred over night. The solvent is removed in vacuo, the residue is partitioned between saturated aqueous NaHCO3 solution (20 mL) and EtOAc (20 mL), the organic layer is washed with water (15 mL), brine (15 mL), and then dried (Na2SO4). Evaporation of the solvent in vacuo provides the product shown above as a yellow oil. Preparative TLC (3:1 Hexane, EtOAc) of the residue provides purified product as a light yellow oil. LC-MS (M+1) 544. 1H NMR (δ, CDCl3) 7.36–7.48 (m, 5H), 7.18 (t, J=7.2 Hz, 1H), 6.70–6.87 (m, 6H), 5.91 (s, 2H), 4.00 (q, J=7.0 Hz, 2H), 3.80 (s, 2H), 3.56 (s, 2H), 3.52 (s, 2H), 2.70 (t, J=7.5 Hz, 2H), 1.41 (t, J=7.2 Hz, 2H), 0.84–1.02 (m, 4H), 0.58 (t, J=7.2 Hz, 3H).

後処理

  1. stirringthe mixture is stirred over night
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between saturated aqueous NaHCO3 solution (20 mL) and EtOAc (20 mL)
  4. washthe organic layer is washed with water (15 mL), brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent in vacuo
  7. customprovides the product
  8. custompurified product as a light yellow oil

出典と根拠

ORDレコード
ord-9702c61f8b384733ab8f00dda36a8e1a
出典データセット
uspto-grants-2007_03
特許番号
US07186734B2

関連ノート

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