2-Methoxy-4-[(1-methylpiperidin-4-yl)oxy]aniline → HCID 73386763, compound

HRID 1480765Notes

Reaction equation

HRID 1480765 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][CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:24]=[CH:23][C:21]=1[NH2:22]>>[CH3:18][O:19][C:20]1[CH:26]=[C:25]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[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 552341692-Methoxy-4-[(1-methylpiperidin-4-yl)oxy]anilineHCID 90000510HCID 90000510, compound

Product 1

HCID 73386763HCID 73386763, compoundYield 5%

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-methoxy-4-(1-methylpiperidin-4-yloxy)aniline at 100° C. for 3 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 followed by 0-10% MeOH in CH2Cl2 and finally eluting with 10% 1M NH3/MeOH in DCM to afford the title compound (5 mg, 5%).

Workup

  1. customThe title compound was prepared
  2. customat 100° C.
  3. customfor 3 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
  7. washfinally eluting with 10% 1M NH3/MeOH in DCM

Sources & evidence

ORD record
ord-eac076d7d9e7488b811a1536043c0d5d
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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