HCID 86617467, compound → HCID 86617466, compound

HRID 2237763Notes

Reaction equation

HRID 2237763 reaction equation
[O-][N+:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]3[CH2:12][C@H:11]([C:13]4[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=4[F:21])[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9][N:8]3[C:4]=2[CH:3]=1.O(Cl)[Cl:33].[P+3]>C(Cl)(Cl)Cl>[Cl:33][C:3]1[C:4]2[N:8]3[CH2:9][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C@@H:11]([C:13]4[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=4[F:21])[CH2:12][C:7]3=[N:6][C:5]=2[CH:30]=[CH:31][N:2]=1

Participants

4

Reactant 2

HCID 86617467HCID 86617467, compoundHCID 178479710HCID 178479710, compound

Product 1

HCID 86617466HCID 86617466, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To the product of Step A in 1.5 mL of chloroform was added 0.008 mL (0.09 mmol) of phosphorus(III) oxychloride and the resultant mixture was refluxed for 1.5 h. The reaction mixture was cooled to ambient temperature, diluted with chloroform (10 mL), and sequentially washed with saturated aqueous sodium bicarbonate solution (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude oil was purified by preparative thin layer chromatography using an Analtech® 1000 micron plate (4% methanol/ethyl acetate) to give the title compound as a viscous oil. LC/MS 453.0 (M+1), 454.8 (M+2).

Workup

  1. washsequentially washed with saturated aqueous sodium bicarbonate solution (5 mL) and brine (5 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude oil was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-48898e79c47a4cd2bcfbe1dbc97a10e1
Source dataset
uspto-grants-2010_05
Patent number
US07718667B2

Reaction notes

Loading…