Cyclopropylamine → N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

HRID 907253Notes

Reaction equation

HRID 907253 reaction equation
C([Mg]Cl)(C)C.[CH3:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=O)=[CH:9][C:8]=1[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][CH:21]=[CH:20]2.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>C1COCC1>[CH:28]1([NH:31][C:11](=[O:13])[C:10]2[CH:15]=[CH:16][C:7]([CH3:6])=[C:8]([C:17]3[CH:26]=[C:25]4[C:24](=[CH:19][CH:18]=3)[C:23](=[O:27])[NH:22][CH:21]=[CH:20]4)[CH:9]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 575518084-Methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzoic acid, methyl ester2×HCID 178418918HCID 178418918, compound

Product 1

HCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of isopropylmagnesium chloride (2M, 0.4 mL) in THF was added dropwise to a stirred solution of 4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzoic acid, methyl ester (Intermediate 3) (76 mg) and cyclopropylamine (0.15 mL) in THF (2 mL). The mixture was stirred for 10 min., quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo and the residue was purified by HPLC to give the title compound as a solid (40 mg).

Workup

  1. customquenched with sat. aqueous NH4Cl
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-9a3c27bdefd8434a95a9d1e673f3b971
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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