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

HRID 747563노트

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HRID 747563 반응식
[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

참가 물질

7

반응물 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)

생성물 1

HCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamide수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-35818c7c2a9e4945bfe580756ae98843
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396843B2

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