N-Methylpropylamine → Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

HRID 14065

Reaction equation

HRID 14065 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.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:35]2[N:36]=[CH:37]C=[CH:39][C:34]=2N=N1.CNCCC>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5]([N:36]([CH3:37])[CH2:35][CH2:34][CH3:39])=[O:7])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 12315N-MethylpropylamineHCID 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 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-iodo-5-(methoxycarbonyl)benzoic acid (1.0 g, 3.3 mmol), prepared as in Example SP-281, step 1, and diisopropylethylamine (1.7 mL, 9.8 mmol) in DMF (10 mL) is added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 1.5 g, 3.9 mmol) then N-methylpropylamine (503 μL, 4.9 mmol). The solution is stirred at room temperature 2 h. The solution is diluted in ethyl acetate and washed with water, saturated sodium bicarbonate, and brine. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound in crude form. This material is purified by flash chromatography (40% ethyl acetate/hexane) to give the purified title compound. MS (ESI) [M+H+]=362.4.

Workup

  1. washwashed with water, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06f535eff89946a9aca5b9bdbe30e5b5
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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