Acetic Acid → HCID 22339741, compound

HRID 585146Notes

Reaction equation

HRID 585146 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]2)[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]=O)[CH:10]=1.C(O)(=O)C.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CN(C)C=O.CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]2)[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:10]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 22339462HCID 22339462, compound

Product 1

HCID 22339741HCID 22339741, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 2-[3,5-dichloro-4-(3-formyl-4-hydroxy-phenoxy)-phenyl]-2H-[1,2,4]triazine-3,5-dione (100 mg) in dichloromethane (3 mL) and dimethylformamide (0.5 mL) was added acetic acid (20 μL), piperidine (35 μL) and sodium triacetoxyborohydride (81 mg). After 6 h, the reaction was diluted into ethyl acetate, washed with saturated sodium bicarbonate, brine, dried (Na2SO4) and concentrated in vacuo to provide a solid mass. Trituration of the solids with ethyl acetate and methanol afforded the title compound of this EXAMPLE as a colorless solid, 73 mg (m.p. 15-217° C.). MS Calc.:463.3; Found:463.0.

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto provide a solid mass

Sources & evidence

ORD record
ord-2198ac405f81483a8c4f31b83c43c887
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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