HCID 22136184, compound → HCID 22136173, compound

HRID 1826827Notes

Reaction equation

HRID 1826827 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:7][CH:6]=1)=[O:4]>O=P(Cl)(Cl)Cl>[C:18]1([C:17]2[N:7]3[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:14]4[C:9]([C:8]3=[CH:15][N:16]=2)=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 22136184HCID 22136184, compound

Product 1

HCID 22136173HCID 22136173, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of the product from part 7 (1.97 g) in 10 ml of POCl3 is stirred at 105° C. for two hours, then cooled and concentrated under vacuum. The residue is treated with EtOAc and washed with saturated aqueous NaHCO3 solution and water. The organic solution is dried over Na2SO4, filtered and then concentrated to afford a solid. Recrystallization from 2-propanol yields the title compound as a yellow solid (0.7 g).

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. additionThe residue is treated with EtOAc
  4. washwashed with saturated aqueous NaHCO3 solution and water
  5. dry with materialThe organic solution is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a solid
  9. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-e9e7c06717dd433ab45e8975bc495050
Source dataset
uspto-grants-2006_05
Patent number
US07053093B2

Reaction notes

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