2,4-Dimethoxyaniline → HCID 73386764, compound

HRID 1480766Notes

Reaction equation

HRID 1480766 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:18][O:19][C:20]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=1[NH2:22]>>[CH3:18][O:19][C:20]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1)[CH:8]=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 176522,4-DimethoxyanilineHCID 90000510HCID 90000510, compound

Product 1

HCID 73386764HCID 73386764, compoundYield 27%

Procedure

The title compound was prepared according to Method 3 (Example 27) using 3-Chloro-5-(1-methyl-1H-pyrazol-4-yl)isoquinoline (Preparation 7) and 2,4-dimethoxyaniline at 80° C. for 1.5 hours followed by 100° C. for 1.5 hours. The reaction mixture was concentrated onto silica gel in vacuo and purified by silica gel column chromatography eluting with 0-100% EtOAc in cyclohexane to afford the title compound (22 mg, 27%).

Workup

  1. customThe title compound was prepared
  2. customat 80° C.
  3. customfor 1.5 hours
  4. concentrationThe reaction mixture was concentrated onto silica gel in vacuo
  5. custompurified by silica gel column chromatography
  6. washeluting with 0-100% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-09b2467568154da78478a38a2313b595
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…