Ethanol → HCID 18452670, compound

HRID 230114Notes

Reaction equation

HRID 230114 reaction equation
[NH2:1][CH2:2][CH:3]([OH:23])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:22])=[O:13])[CH2:7][CH2:6]1.C(N(CC)CC)C.[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Cl.C([OH:42])C>>[CH3:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[NH:14][C:12](=[O:13])[CH2:11][N:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH:3]([OH:23])[CH2:2][NH:1][C:34]([C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[F:31])=[O:42])[CH2:6][CH2:7]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 18519838HCID 18519838, compound

Product 1

HCID 18452670HCID 18452670, compound

Conditions

Temperature
90 °C

Procedure

To a solution of 2-[4-(3-amino-2-hydroxypropyl)piperazin-1-yl]-N-(2,6-dimethylphenyl)-acetamide (0.312 mmoles) in ethanol (2 mL) was added triethylamine (100 μL) followed by 2-fluorobenzyl chloride (0.312 mmoles), and the solution was stirred at 90° C. for 18 hours. Solvent was removed under reduced pressure, and the residue purified by preparative TLC, eluting with 5% methanol/dichloromethane, to yield N-(2,6-dimethylphenyl)-2-(4-{3-[(2-fluorophenyl)-carbonylamino]-2-hydroxypropyl}piperazinyl)acetamide, a compound of Formula I.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by preparative TLC
  3. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-42d617eaeacd4462b37f7763157128c5
Source dataset
uspto-grants-2009_07
Patent number
US07566717B2

Reaction notes

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