Sodium Hydroxide → 4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide

HRID 491873Notes

Reaction equation

HRID 491873 reaction equation
[NH2:1][CH:2]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:3][CH2:4][C:5]([N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:8][CH2:9][OH:10])=[O:6].[N+:23]([C:26]1[C:27]([CH:39]=O)=[CH:28][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:30][CH:31]=1)([O-:25])=[O:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[CH:17]1([CH:2]([NH:1][CH2:39][C:27]2[C:26]([N+:23]([O-:25])=[O:24])=[CH:31][N:30]=[C:29]([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:28]=2)[CH2:3][CH2:4][C:5]([N:7]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:8][CH2:9][OH:10])=[O:6])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 670234664-amino-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide

Product 1

HCID 670236094,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-amino-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide (2.0 g, 6.5 mmol) and 5-nitro-2-phenoxypyridine-4-carbaldehyde (1.6 g, 6.5 mmol) in 1,2 dichloroethane (50 mL), NaBH(OAc)3 (2.0 g, 9.4 mmol) was added, and the reaction mixture was stirred at room temperature overnight. After the addition of 1N NaOH solution, the reaction mixture was then extracted with EtOAc (200 mL×2). The organic layer was dried with Mg2SO4 and then evaporated to a residue which was purified by column chromatography to yield 4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide as an oil.

Workup

  1. extractionthe reaction mixture was then extracted with EtOAc (200 mL×2)
  2. dry with materialThe organic layer was dried with Mg2SO4
  3. customevaporated to a residue which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-587f9a63548a4741bf5ef7ec41704ff9
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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