Hydrochloric Acid → HCID 178527155, compound

HRID 851897Notes

Reaction equation

HRID 851897 reaction equation
[O:1]=[S:2]1(=[O:25])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[CH:15][CH:14]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:22][CH2:23][CH2:24][CH:4]2[NH:3]1.[N-:26]=[N+:27]=[N-:28].[Na+].[NH4+].[Cl-].Cl>CN(C=O)C>[NH:26]1[C:20]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][C:9]3[CH:10]=[CH:11][C:6]4[N:5]5[CH2:22][CH2:23][CH2:24][CH:4]5[NH:3][S:2](=[O:1])(=[O:25])[C:7]=4[CH:8]=3)=[CH:14][CH:15]=2)=[N:21][N:28]=[N:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69199240{4-[(5,5-Dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}acetonitrile

Product 1

HCID 178527155HCID 178527155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 300 mg (0.844 mmol) of the product obtained in Step A, 164 mg (2.53 mmol) of sodium azide and 113 mg (2.11 mmol) of NH4Cl in 3 ml of DMF is stirred at 110° C. for 24 hours. The reaction mixture is allowed to return to ambient temperature and is poured into 20 ml of 1N HCl. Extraction (AcOEt), drying (MgSO4) and evaporating to dryness are carried out. The residue is triturated in Et2O and the precipitate is filtered off to yield the title product.

Workup

  1. customto return to ambient temperature
  2. extractionExtraction (AcOEt)
  3. dry with materialdrying (MgSO4)
  4. customevaporating to dryness
  5. customThe residue is triturated in Et2O
  6. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-5fd29ee5980e434f944cdd8222fb58c5
Source dataset
uspto-grants-2007_08
Patent number
US07253162B2

Reaction notes

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