Methanol → HCID 25207743, compound

HRID 1594010Notes

Reaction equation

HRID 1594010 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1N=NC(N2CC[O:29][CH2:28][CH2:27]2)=CC=1C1C=CC=CC=1.[CH3:38][CH2:39][O:40][C:41]([CH3:43])=[O:42].[CH3:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].C[OH:51]>C(Cl)Cl.[Pd]>[CH2:39]([O:40][C:41]([C:43]1[C:45]([C:44]([O:29][CH2:28][CH3:27])=[O:51])=[C:46]([CH2:47][CH:48]=[CH2:49])[N:11]2[C:12]=1[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:8][C:9]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[N:10]2)=[O:42])[CH3:38]

Participants

7

Reactant 4

HCID 887MethanolHCID 11716038HCID 11716038, compoundHCID 21226206Ethyl acetate hexaneHCID 69448414HCID 69448414, compound

Product 1

HCID 25207743HCID 25207743, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
48 °C

Procedure

4-(5-Phenylpyridazin-3-yl)morpholine. A mixture of 4-(6-Chloro-5-phenylpyridazin-3-yl)morpholine (9.91 g, 35.9 mmol), HCO2NH4 (22.7 g, 0.359 mol), and 10% Pd/C (2 g) in MeOH (200 mL) was heated at 48° C. for 16 h. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to provide a yellow solid. The solid was dissolved in CH2Cl2 and washed with water, dried over MgSO4, filtered, and concentrated in vacuo to provide a yellow solid. The title compound was obtained by recrystallization from EtOAc/hexane. 1H NMR (DMSO-d6) δ 3.75 (s, 8H), 7.64 (m, 3H), 8.01 (m, 2H), 8.23 (s, 1H), 9.63 (s, 1H). Mass Spectrum (ESI+) m/e=242.2 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto provide a yellow solid
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a yellow solid

Sources & evidence

ORD record
ord-f4db24cff99642ba93688bccba182992
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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