Cyclopropylamine → N-Cyclopropyl-3-iodo-4-methylbenzamide

HRID 747563ノート

反応式

HRID 747563 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.CN(C(ON1N=NC2[CH:23]=[CH:24][CH:25]=[N:26]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:25]1([NH:26][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=2)[CH2:23][CH2:24]1

参加物

7

反応物 5

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamide収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Iodo-4-methylbenzoic acid (5 g, 19.1 mmol) and HATU (8.71 g, 22.9 mmol) in DMF (25 ml) were stirred at room temperature for 10 minutes. HOBT (2.58 g, 19.1 mmol), cyclopropylamine (1.37 g, 22.9 mmol) and DIPEA (2.5 ml, 57.3 mmol) were added and stirring continued for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (100 ml) and aqueous sodium carbonate (1M, 75 ml). The aqueous layer was extracted with DCM (50 ml) and the combined organic phases washed with brine (75 ml) and dried (magnesium sulphate). The solution was absorbed onto silica and purified by chromatography on silica eluting with ethyl acetate/cyclohexane (1:3). The product fractions were reduced to dryness under vacuum to give N-cyclopropyl-3-iodo-4-methylbenzamide (4.7 g, 82%). LCMS: retention time 3.09 min, MH+302.

後処理

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (100 ml) and aqueous sodium carbonate (1M, 75 ml)
  3. extractionThe aqueous layer was extracted with DCM (50 ml)
  4. washthe combined organic phases washed with brine (75 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customThe solution was absorbed onto silica
  7. custompurified by chromatography on silica eluting with ethyl acetate/cyclohexane (1:3)

出典と根拠

ORDレコード
ord-35818c7c2a9e4945bfe580756ae98843
出典データセット
uspto-grants-2008_07
特許番号
US07396843B2

反応ノート

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