Sodium hydride → HCID 86618536, compound

HRID 2426543Notes

Reaction equation

HRID 2426543 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:16][CH2:17][CH3:18].[H-].[Na+].[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([CH3:29])=[CH:24][N:23]=1>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:24]3[C:25]([CH3:29])=[CH:26][N:27]=[C:22]([Cl:21])[N:23]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamine2×

Product 1

HCID 86618536HCID 86618536, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamine (40.3 mg, 0.15 mmol, 1.2 equiv; intermediate A2) in dry DMF (1.5 mL) was added sodium hydride (6.6 mg, 0.15 mmol, 1.2 equiv; 55% free-flowing powder moistened with oil) and the reaction mixture stirred at rt under Ar. After 2 h, 2,4-dichloro-5-methyl-pyrimidine (20.4 mg, 0.125 mmol, 1.0 equiv; commercially available) was added and the mixture heated to 120° C. for 48 h. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 3.7 mg (8%) of the title compound. MS (ISP): 395.2 [M+H]+.

Workup

  1. additioncommercially available) was added
  2. temperaturethe mixture heated to 120° C. for 48 h
  3. customRemoval of the solvent
  4. customunder reduced pressure and purification by preparative HPLC on reversed phase
  5. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-b643257195bc49f3a07461eeb2169a2a
Source dataset
uspto-grants-2011_06
Patent number
US07968568B2

Reaction notes

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