N-Methylpropylamine → Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoate

HRID 1454190ノート

反応式

HRID 1454190 の反応式
[Br: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.CN(C(ON1N=NC2[CH:26]=[CH:27][CH:28]=[N:29][C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNCCC>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:7])[N:29]([CH3:24])[CH2:28][CH2:27][CH3:26])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

参加物

6

反応物 3

HCID 12315N-MethylpropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

生成物 1

HCID 57529325Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoate収率 99%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-bromo-5-(methoxycarbonyl)benzoic acid (1.0 g, 3.86 mmol) and HATU (1.76 g, 4.63 mmol) in DMF (35 mL) was stirred at room temperature for 10 min. Then N-methylpropan-1-amine (0.28 g, 0.4 mL, 3.86 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O (3 times) and brine, dried over sodium sulfate, and concentrated under vacuum to give the title compound (1.2 g, 99% yield): HPLC retention time: 1.89 min (method A). MS (ESI) (M+H)+ 314.03.

後処理

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washwashed with H2O (3 times) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-0e9b3be59a034d37870358af773d3cad
出典データセット
uspto-grants-2009_01
特許番号
US07476764B2

反応ノート

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