Hydrochloric Acid → 3-{4-[(5,5-Dioxido-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]benzyl}-1,2,4-oxadiazole-5(4H)-thione

HRID 851899Notes

Reaction equation

HRID 851899 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].C1CCN2C(=NCCC2)CC1.[O:24]=[S:25]1(=[O:50])[C:30]2[CH:31]=[C:32]([O:35][C:36]3[CH:41]=[CH:40][C:39]([CH2:42][C:43](=[N:45][OH:46])[NH2:44])=[CH:38][CH:37]=3)[CH:33]=[CH:34][C:29]=2[N:28]2[CH2:47][CH2:48][CH2:49][C:27]2=[N:26]1.Cl>CC#N>[O:50]=[S:25]1(=[O:24])[C:30]2[CH:31]=[C:32]([O:35][C:36]3[CH:37]=[CH:38][C:39]([CH2:42][C:43]4[NH:44][C:1](=[S:2])[O:46][N:45]=4)=[CH:40][CH:41]=3)[CH:33]=[CH:34][C:29]=2[N:28]2[CH2:47][CH2:48][CH2:49][C:27]2=[N:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 802641,1'-ThiocarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 878716182-{4-[(5,5-Dioxido-2,3-dihydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}-n'-hydroxyethanimidamide

Product 1

HCID 1785271573-{4-[(5,5-Dioxido-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]benzyl}-1,2,4-oxadiazole-5(4H)-thione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

348 mg (1.95 mmol) of 1,1′-thiocarbonyldiimidazole and then 530 μl (3.516 mmol) of DBU are added to a suspension of the product obtained in Step A (330 mg, 0.85 mmol) in 8 ml of CH3CN. The reaction solution is stirred at ambient temperature overnight. 20 ml of 1N HCl are added; extraction (CH2Cl2), washing (saturated NaCl), drying (MgSO4) and evaporating to dryness are carried out. The title product is obtained in the form of a yellow wax which is used in the crude state in the following Step.

Workup

  1. extractionextraction (CH2Cl2)
  2. washwashing (saturated NaCl)
  3. dry with materialdrying (MgSO4)
  4. customevaporating to dryness

Sources & evidence

ORD record
ord-48032f630b6f4bc99aea3f064dd675c2
Source dataset
uspto-grants-2007_08
Patent number
US07253162B2

Reaction notes

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