1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine → HCID 68782108, compound

HRID 2264399Notes

Reaction equation

HRID 2264399 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)[CH3:22]>CC(N(C)C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[N:8]=[C:7]([NH:34][CH:31]2[CH2:32][CH2:33][N:28]([CH2:27][C:26]3[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:24]([O:23][CH2:21][CH3:22])[CH:25]=3)[CH2:29][CH2:30]2)[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×HCID 86615292HCID 86615292, compound

Product 1

HCID 68782108HCID 68782108, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-chloro-6-(2,4-dichloro-phenoxy)-pyrimidine-4-carboxylic acid methyl ester (50.0 mg, 0.15 mmol, 1.0 equiv) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.2 equiv; intermediate A1) in DMAc (2 mL) was heated by microwave irradiation to 180° C. for 15 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 15.0 mg (15%) of the title compound. MS (ISP): 561.2 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-86297faec1974ab280fa74bcc4cf37dc
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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