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

HRID 14065

反応式

HRID 14065 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-06f535eff89946a9aca5b9bdbe30e5b5
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

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