Sodium Hydroxide → 3,N-Dimethyl-2-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-phenethyl-butyramide

HRID 491916Notes

Reaction equation

HRID 491916 reaction equation
[NH2:1][CH:2]([CH:15]([CH3:17])[CH3:16])[C:3]([N:5]([CH3:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[N+:18]([C:21]1[C:22]([CH:34]=O)=[CH:23][C:24]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:25][CH:26]=1)([O-:20])=[O:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1COCC1.ClCCl>[CH3:16][CH:15]([CH3:17])[CH:2]([NH:1][CH2:34][C:22]1[C:21]([N+:18]([O-:20])=[O:19])=[CH:26][N:25]=[C:24]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:23]=1)[C:3]([N:5]([CH3:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 548719212-Amino-3,N-dimethyl-N-phenethyl-butyramideHCID 576783284-Formyl-5-nitro-2-phenoxypyridine

Product 1

HCID 670236673,N-Dimethyl-2-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-phenethyl-butyramide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-3,N-dimethyl-N-phenethyl-butyramide (1.5 g, 6.48 mmol), 5-nitro-2-phenoxy-pyridine-4-carbaldehyde (1.5 g, 6.1 mmol), dichloromethane (75 mL), and THF (75 mL) was stirred for 5 hrs. Sodium triacetoxyborohydride (3.0 g, 14.25 mmol) was then added and the resulting mixture was stirred 16 hrs. Sodium hydroxide solution ([0.1 N], 100 mL) was added, the organic layer was separated, treated with MgSO4, filtered and the solvent evaporated to yield an oil. The oil was purified by column chromatography (10%-40% ethyl acetate/heptane) to yield a residue.

Workup

  1. stirringthe resulting mixture was stirred 16 hrs
  2. customthe organic layer was separated
  3. additiontreated with MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customto yield an oil
  7. customThe oil was purified by column chromatography (10%-40% ethyl acetate/heptane)
  8. customto yield a residue

Sources & evidence

ORD record
ord-2b32a94374914e2f9639b51bf3adbe71
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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