Acetic Acid → HCID 69216913, compound

HRID 2221812Notes

Reaction equation

HRID 2221812 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:36])=[C:9]([CH2:11][O:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][O:18][C:19]3[C:23]([CH:24]=O)=[CH:22][N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]=3)=[CH:15][C:14]=2[O:34][CH3:35])[N:10]=1.CN.C(O)(=O)C.[B-][C:44]#[N:45].[Na+]>O1CCCC1.C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:36])=[C:9]([CH2:11][O:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][O:18][C:19]3[C:23]([CH2:24][NH:45][CH3:44])=[CH:22][N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]=3)=[CH:15][C:14]=2[O:34][CH3:35])[N:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 20587905Sodium cyanoborohydride [MI]HCID 866057753-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 69216913HCID 69216913, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde (1.0 g), methylamine (2M tetrahydrofuran solution, 3.2 mL), acetic acid (0.13 g), ethanol (20 mL) and tetrahydrofuran (20 mL) was stirred at room temperature for 2 hrs. Sodium cyanotrihydroborate (0.20 g) was added to the reaction mixture, and the mixture was further stirred at room temperature for 3 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give N-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}methyl)-N-methylamine as colorless crystals (0.15 g, yield 14%) from a fraction eluted with ethyl acetate-methanol (10:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 103-104° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 3 hrs
  2. concentrationThe reaction mixture was concentrated
  3. additionethyl acetate was added to the residue
  4. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f67e88e60d0419abe33c1b08396e726
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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