Hydrochloric Acid → HCID 69523007, compound

HRID 851906Notes

Reaction equation

HRID 851906 reaction equation
[O:1]=[S:2]1(=[O:25])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16](O)=[O:17])[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:22][CH2:23][CH2:24][C:4]2=[N:3]1.C(Cl)(=O)C(Cl)=O.C[CH2:33][N:34](CC)[CH2:35]C.CNC.Cl>C(Cl)Cl.CN(C=O)C.C1COCC1>[O:1]=[S:2]1(=[O:25])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([N:34]([CH3:35])[CH3:33])=[O:17])[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:22][CH2:23][CH2:24][C:4]2=[N:3]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 691986953-[(2,3-Dihydro-5,5-dioxido-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)-oxy]benzoic acid

Product 1

HCID 69523007HCID 69523007, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the product obtained in Step C (1.40 g, 3.91 mmol) in 20 ml of CH2Cl2 there are added 2 drops of DMF and then, dropwise, 684 μl (7.81 mmol) of oxalyl chloride diluted with 2 ml of CH2Cl2. Stirring is carried out at ambient temperature for 2 hours 30 minutes; evaporation to dryness is carried out; the residue is taken up in 15 ml of CH2Cl2; 1.1 ml (7.81 mmol) of Et3N and then 2.94 ml (5.87 mmol) of a 2M solution of dimethylamine in THF are added. Stirring is carried out at ambient temperature for 1 hour. The reaction mixture is acidified with 0.5N HCl and extracted (CH2Cl2). The organic phases are combined, washed (saturated NaCl), dried (MgSO4) and evaporated. The residue is triturated in Et2O; the title product precipitates out and is recovered by filtration. Elemental micro-analysis:

Workup

  1. customevaporation to dryness
  2. stirringStirring
  3. waitis carried out at ambient temperature for 1 hour
  4. extractionextracted (CH2Cl2)
  5. washwashed (saturated NaCl)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue is triturated in Et2O
  9. customthe title product precipitates out
  10. filtrationis recovered by filtration

Sources & evidence

ORD record
ord-b82fe9914c7a4a6d99811ccc9fbbf318
Source dataset
uspto-grants-2007_08
Patent number
US07253162B2

Reaction notes

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