Hydrochloric Acid → HCID 178527155, compound

HRID 29775Notes

Reaction equation

HRID 29775 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-5aa3db3d1e814a458a1f7123b4efb822
Source dataset
uspto-grants-2008_09
Patent number
US07423034B2

Reaction notes

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