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

HRID 1620013Notes

Reaction equation

HRID 1620013 reaction equation
[CH2:1]([CH:3]1[CH2:8][C:7](=[O:9])[NH:6][N:5]=[C:4]1[C:10]1[CH:28]=[CH:27][C:13]2[N:14]=[C:15]([C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH:23]=O)=[CH:19][CH:18]=3)[O:16][C:12]=2[CH:11]=1)[CH3:2].C(O)(=O)C.[CH3:33][CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.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:28]=[CH:27][C:13]3[N:14]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([O:21][CH2:22][CH2:23][N:37]5[CH2:38][CH2:39][CH:34]([CH3:33])[CH2:35][CH2:36]5)=[CH:25][CH:26]=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 693814-MethylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86689077{4-[6-(4-Ethyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-phenoxy}-acetaldehyde

Product 1

HCID 674659055-ethyl-6-(2-{4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenyl}-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

11 mg (29 μmol) {4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-phenoxy}-acetaldehyde are placed in 2 mL DCM and 250 μL DMF. 1.70 μL (29 mmol) acetic acid and 3 μL (42 μmol) 4-methylpiperidine are added and the mixture is stirred for 20 min at RT. Then 9 mg (42 μmol) sodium triacetoxyborohydride are added and the mixture is stirred overnight 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 KG. (DCM/MeOH+ammonia) the solv. of the corresponding fractions is eliminated i.V. and the residue is crystallised from EN petroleum ether.

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. extractionextracted successively with 10% sodium carbonate solution and sat. saline solution
  3. customand the residue is purified through KG
  4. customand the residue is crystallised from EN petroleum ether

Sources & evidence

ORD record
ord-81d0e8ff687649fa96c4fca797e149cf
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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