Dicyclohexylcarbodiimide → HCID 89524829, compound

HRID 920227Notes

Reaction equation

HRID 920227 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][N:2]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:18][O:17][N:16]([CH3:15])[C:11]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:1]=[N:2][CH:3]=[CH:4]2)=[O:13]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 21393830Isoquinoline-8-carboxylic acid

Product 1

HCID 89524829HCID 89524829, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Commercially available isoquinoline-8-carboxylic acid (0.4 g, 2.31 mmol), N,O-dimethylhydroxylamine hydrochloride (0.45 g, 4.62 mmol), DMAP (0.28 g, 2.31 mmol), and polymer-supported DCC (0.71 g, 3.46 mmol) were charged in a 50 mL round bottom flask. Then anhydrous THF (23 mL) was added. The reaction was stirred overnight at RT. The reaction mixture was filtered and filtrate was concentrated. Purification by normal phase chromatography (0-50% EtOAc in hexane) yielded N-methoxy-N-methylisoquinoline-8-carboxamide (14-2).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationfiltrate was concentrated
  3. customPurification by normal phase chromatography (0-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-faef751fdf6249b28a13bcc448b745e9
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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