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

HRID 1643200

반응식

HRID 1643200 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2779e7bd431a4691acf3fa559f2e199b
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119665B2

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