Acetic Acid → 5-ethyl-6-{2-[4-(2-hydroxy-1-methyl-ethoxy)-phenyl]-benzoxazol-6-yl}-4,5-dihydro-2H-pyridazin-3-one

HRID 1620016Notes

Reaction equation

HRID 1620016 reaction equation
[CH2:1]([CH:3]1[CH2:8][C:7](=[O:9])[NH:6][N:5]=[C:4]1[C:10]1[CH:29]=[CH:28][C:13]2[N:14]=[C:15]([C:17]3[CH:27]=[CH:26][C:20]([O:21][CH:22]([CH3:25])[CH:23]=[O:24])=[CH:19][CH:18]=3)[O:16][C:12]=2[CH:11]=1)[CH3:2].C(O)(=O)C.C(NC(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([CH:3]1[C:4]([C:10]2[CH:29]=[CH:28][C:13]3[N:14]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([O:21][CH:22]([CH3:25])[CH2:23][OH:24])=[CH:26][CH:27]=4)[O:16][C:12]=3[CH:11]=2)=[N:5][NH:6][C:7](=[O:9])[CH2:8]1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86689078HCID 86689078, compound

Product 1

HCID 674648265-ethyl-6-{2-[4-(2-hydroxy-1-methyl-ethoxy)-phenyl]-benzoxazol-6-yl}-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

40 mg (102 μmol) 2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-phenoxy}-propionaldehyde are placed in 2 mL DCM and 250 μL DMF. 6 μL (104 mmol) acetic acid and 22 μL (156 μmol) diisopropylamine are added and the mixture is stirred for 40 min at RT. Then 33 mg (156 μmol) sodium triacetoxyborohydride are added and the mixture is stirred for 3.5 h at RT. The reaction mixture is diluted with DCM and extracted successively with 10% sodium carbonate solution and sat. saline solution. The solv. of the organic phase is eliminated i.V. and the residue is purified through HPLC. (xBridge, MeOH/H2O+TFA) The corresponding fractions are freeze-dried.

Workup

  1. stirringthe mixture is stirred for 3.5 h at RT
  2. extractionextracted successively with 10% sodium carbonate solution and sat. saline solution
  3. customand the residue is purified through HPLC
  4. dry with material(xBridge, MeOH/H2O+TFA) The corresponding fractions are freeze-dried

Sources & evidence

ORD record
ord-a77ccf7ca34f45fd96fc2387c8e2b5a3
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

Loading…