Isopropylamine → 6-Isopropylamino-5-methyl-nicotinic acid isopropyl ester

HRID 1908786Notes

Reaction equation

HRID 1908786 reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9](Cl)=[N:8][CH:7]=1)([CH3:3])[CH3:2].[CH:15]([NH2:18])([CH3:17])[CH3:16]>O1CCOCC1>[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH:18][CH:15]([CH3:17])[CH3:16])=[N:8][CH:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 866505246-Chloro-5-methylnicotinic acid isopropyl ester

Product 1

HCID 670269016-Isopropylamino-5-methyl-nicotinic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-chloro-5-methyl-nicotinic acid isopropyl ester (200 mg, 0.936 mmol) in dioxane (5 mL) and isopropylamine (3 mL) is stirred in a sealed vial at 100° C. for 1 week. The solvent is evaporated and the residue dissolved in DCM (50 mL) and washed with sat. aq. NaHCO3 solution (20 mL). The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates with heptane:EA 1:1 to give 6-isopropylamino-5-methyl-nicotinic acid isopropyl ester (137 mg) as a yellow oil; LC-MS: tR=0.68 min, [M+1]+=237.02.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in DCM (50 mL)
  3. washwashed with sat. aq. NaHCO3 solution (20 mL)
  4. extractionextract
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-a45005a6ac764edf969c0a5f5d199ec4
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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