Dimethylamine → HCID 21791173, compound

HRID 1626923Notes

Reaction equation

HRID 1626923 reaction equation
N[C:2]1[N:7]=[C:6](N[C@H](C2N(C3C=CC=CC=3)C(=O)C3C(C=2)=CC=CC=3C2C=CN=C(OC)C=2)C)[C:5]([C:36]([OH:38])=O)=[CH:4][N:3]=1.[CH2:39]([N:41]=[C:42]=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.CNC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:39][N:41]([CH3:42])[C:36]([C:5]1[CH:6]=[N:7][CH:2]=[N:3][CH:4]=1)=[O:38]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 71269849HCID 71269849, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 21791173HCID 21791173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-amino-4-((1-(8-(2-methoxypyridin-4-yl)-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)-pyrimidine-5-carboxylic acid (44 mg, 0.087 mmol) in anhydrous N,N-dimethylmethanamide (3 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (25 mg, 0.13 mmol) and hydroxybenzotriazole (18 mg, 0.13 mmol) were added and the resulting mixture was stirred at RT for 30 min. To this mixture, dimethylamine (2M in THF, 0.065 mL, 0.13 mmol) and N,N-diisopropylethylamine (0.040 mL, 0.19 mmol) were added and the reaction mixture was stirred at RT for 3 h. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product 112, (S)-2-amino-441-(8-(2-methoxypyridin-4-yl)-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)-N,N-dimethylpyrimidine-5-carboxamide. ESI-MS m/z: 533.8 [M−H]+.

Workup

  1. stirringthe reaction mixture was stirred at RT for 3 h
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-10f27fc3c8994f4f907db5269f83e880
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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