Lithium Hydroxide → HCID 17989733, compound

HRID 917309Notes

Reaction equation

HRID 917309 reaction equation
[OH-].[Li+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=4)[N:23]=2)[N:20]=[CH:19][CH:18]=[CH:17]3)[CH2:10][CH2:9]1)=[O:7])C>O.CN1C(=O)CCC1>[C:30]([C:26]1[CH:25]=[C:24]([C:22]2[N:23]=[C:14]([CH:11]3[CH2:10][CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]3)[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:29]=[CH:28][CH:27]=1)#[N:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 24738505HCID 24738505, compound

Product 1

HCID 17989733HCID 17989733, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of lithium hydroxide (6.5 mg, 0.155 mmol) in water (160 μl) is added to a solution of 4-[8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexane carboxylic acid ethyl ester (60 mg, 0.155 mmol) in NMP(0.16 ml). Upon completion, the reaction is diluted with water and washed with ethyl acetate (5 ml). The aqueous layer is acidified with 5% citric acid and the product is extracted into ethyl acetate. The organic layer is dried over brine (10 ml) and anhydrous MgSO4, filtered and evaporated. Purification by flash chromatography using Keiselgel 40-63 grade silica and eluting with 1.5% CH3OH:0.5% CH3COOH: dichloromethane affords the title compound. MH+ 357.0. mp 179.8-180.3° C.

Workup

  1. washwashed with ethyl acetate (5 ml)
  2. extractionthe product is extracted into ethyl acetate
  3. dry with materialThe organic layer is dried over brine (10 ml) and anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography
  7. washeluting with 1.5% CH3OH

Sources & evidence

ORD record
ord-da9bcbc8d84a4b15858da640fab0d53b
Source dataset
uspto-grants-2007_09
Patent number
US07273875B2

Reaction notes

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