Ethyl Acetate → HCID 10138086, compound

HRID 2211666Notes

Reaction equation

HRID 2211666 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:17].[CH3:24][CH2:25][O:26][C:27](C)=[O:28]>>[O:28]1[C:24]2[CH:22]=[CH:23][C:18]([CH2:16][NH:15][C:19]3[C:18]([C:16]([NH:15][C:3]4[CH:4]=[CH:5][C:6]([O:8][C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=5)=[CH:7][CH:2]=4)=[O:17])=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:19][C:25]=2[O:26][CH2:27]1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 131725910HCID 131725910, compound

Product 1

HCID 10138086HCID 10138086, compound

Conditions

Temperature
110 °C

Procedure

2-Chloro-(3-pyridyl)-N-(4-phenoxyphenyl)-carboxamide (0.500 g, 1.5 mmol) and 2H-benzo[d]1,3-dioxolan-5-ylmethylamine (0.680 g, 4.5 mmol) were combined and heated neat at 110° C. for 18 h. After cooling to RT, the resulting residue was dissolved in EtOAc and washed with saturated NaACO3 solution and brine, respectively. The organics were dried over Na2SO4 and evaporated. The crude material was purified by column chromatography with EtOAc/hexanes (1:2) as eluant to leave the desired compound as an off-white solid. MS: (ES+) 440 (M +1)+; (ES−): 438 (M−1)−. Calc'd. for C26H21N3O4-439.15.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with saturated NaACO3 solution and brine
  3. dry with materialThe organics were dried over Na2SO4
  4. customevaporated
  5. customThe crude material was purified by column chromatography with EtOAc/hexanes (1:2) as eluant

Sources & evidence

ORD record
ord-4fc4040e0a294537a67304adb735eddb
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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