N-Methylbutylamine → Methyl 3-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate

HRID 349086

Reaction equation

HRID 349086 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=N[C:34]2[CH:35]=[CH:36][CH:37]=[N:38][C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNCCCC>CN(C=O)C>[CH2:37]([N:38]([CH3:33])[C:5]([C:4]1[CH:8]=[C:9]([CH:10]=[C:2]([I:1])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7])[CH2:36][CH2:35][CH3:34]

Participants

6

Reactant 4

HCID 8068N-MethylbutylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 21086165Methyl 3-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-methylbutylamine (581 μL, 4.9 mmol) are added. The reaction stirred at room temperature 2 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+.

Workup

  1. customThe reaction is partitioned between ethyl acetate and water
  2. washThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8a500f39426944db86cb3eecd30559c4
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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