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

HRID 907260Notes

Reaction equation

HRID 907260 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=4[CH3:28])[C:21]([O:23]C)=O)[CH:14]=3)[C:9]2=[O:29])=[CH:5][CH:4]=1.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.C([Mg]Cl)(C)C>O1CCCC1>[CH:32]1([NH:35][C:21](=[O:23])[C:20]2[CH:25]=[CH:26][C:27]([CH3:28])=[C:18]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[C:9](=[O:29])[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:31][CH:30]=3)[CH:17]=[CH:16]4)[CH:19]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 575517473-[2-(4-Methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-4-methyl-benzoic acid, methyl ester2×HCID 178418918HCID 178418918, compound

Product 1

HCID 25020726N-Cyclopropyl-3-[2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-4-methyl-benzoic acid, methyl ester (product of step v)) (1.0 g) and cyclopropylamine (0.71 g) in tetrahydrofuran (3 mL) was treated with isopropylmagnesium chloride (2M in THF, 0.77 mL) and stirred at room temperature for 1 hour. The reaction mixture was quenched with aqueous ammonium chloride and extracted into ethyl acetate. The organic phase was dried, filtered and evaporated to yield the title compound as a solid (850 mg).

Workup

  1. customThe reaction mixture was quenched with aqueous ammonium chloride
  2. extractionextracted into ethyl acetate
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cf241381208d4750a61d190d69432d65
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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