Phosphorus oxychloride → HCID 22479180, compound

HRID 2182613Notes

Reaction equation

HRID 2182613 reaction equation
O=P(Cl)(Cl)Cl.[C:6]([C:8]1[CH:36]=[CH:35][C:11]([CH2:12][C:13]23[CH2:20][CH2:19][CH2:18][N:17]2[C:16](=[O:21])[N:15]([C:22]2[CH:27]=[C:26]([N:28]4[CH:32]=[CH:31][CH:30]=[CH:29]4)[CH:25]=[C:24]([Cl:33])[CH:23]=2)[C:14]3=[O:34])=[CH:10][CH:9]=1)#[N:7].[C:37]([O-])(O)=[O:38].[Na+]>CN(C=O)C.O.C(Cl)Cl>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][C:13]23[CH2:20][CH2:19][CH2:18][N:17]2[C:16](=[O:21])[N:15]([C:22]2[CH:27]=[C:26]([N:28]4[CH:32]=[CH:31][CH:30]=[C:29]4[CH:37]=[O:38])[CH:25]=[C:24]([Cl:33])[CH:23]=2)[C:14]3=[O:34])=[CH:35][CH:36]=1)#[N:7]

Participants

7

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 22479105HCID 22479105, compound

Product 1

HCID 22479180HCID 22479180, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of POCl3 (0.1 mL) and DMF (0.3 mL) was added after 45 minutes a solution of 5-(4-cyanobenzyl)-3-[3-chloro-5-(1-pyrrolyl)-phenyl]-1,3-diazabicyclo[3.3.0)octane-2,4-dione (0.22 g) in DMF (0.5 mL). After 1 hour at room temperature, the reaction mixture was diluted with water (2 mL) and stirred. After 30 minutes, the mixture was diluted with CH2Cl2 and satd. NaHCO3. The organic layer was collected, washed with brine, dried (Na2SO4), filtered and concentrated. Purification by chromatography (silica gel: EtOAc/hexane: 1/3, Chromatotron) afforded 0.091 g of the titled compound. MS (m/z) 459 (MH+). mp 109.7° C.

Workup

  1. waitAfter 30 minutes
  2. customThe organic layer was collected
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica gel: EtOAc/hexane: 1/3, Chromatotron)

Sources & evidence

ORD record
ord-270674299c774363a0fa155874c729fb
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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