Hexane → HCID 18437772, compound

HRID 1643201Notes

Reaction equation

HRID 1643201 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl.[CH2:30]([C:34]1[C:35]([CH2:47]Cl)=[C:36]([Cl:46])[N:37]=[N:38][C:39]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:31][CH2:32][CH3:33].CCCCCC>CC#N.CCOC(C)=O>[CH2:30]([C:34]1[C:35]([CH2:47][N:12]([CH2:11][C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=2)=[C:36]([Cl:46])[N:37]=[N:38][C:39]=1[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 18437826HCID 18437826, compoundHCID 18438115HCID 18438115, compound

Product 1

HCID 18437772HCID 18437772, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(3-ethoxy-benzyl)-amine (0.211 g, 0.7 mmol) and K2CO3 (0.69 g, 3 mmol) is added to a solution of 5-butyl-3-chloro-4-chloromethyl-6-phenyl-pyridazine hydrochloride (0.175 g, 0.6 mmol) in CH3CN (15 mL). The mixture is stirred at 80° C. overnight. The solvent is removed in vacuo and the residue is partitioned between water (20 mL) and EtOAc (20 mL). The organic layer is washed with water (15 mL), brine (15 mL), then dried (Na2SO4). Evaporation of the solvent in vacuo provides a yellow oil. Preparative TLC (3:1 Hexane, EtOAc) of the residue provides a light yellow oil. LC-MS (M+1) 558 1H NMR (δ, CDCl3) 7.36-7.48 (m, 5H), 7.18 (t, J=7.2 Hz, 1H), 6.72-6.89 (m, 6H), 4.21 (s, 4H), 4.01 (q, J=7.2 Hz, 2H), 3.80 (s, 2H), 3.56 (s, 2H), 3.50 (s, 2H), 2.70 (t, J=7.2 Hz, 2H), 1.41 (t, J=6.9 Hz, 3H), 0.84-1.02 (m, 4H), 0.58 (t, J=7.2 Hz, 3H).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (20 mL) and EtOAc (20 mL)
  3. washThe organic layer is washed with water (15 mL), brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent in vacuo
  6. customprovides a yellow oil

Sources & evidence

ORD record
ord-144ee1c2422d4169a43cc5a5913b1551
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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