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

HRID 851892Notes

Reaction equation

HRID 851892 reaction equation
[O:1]=[S:2]1(=[O:26])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([NH:18][NH2:19])=[O:17])[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:23][CH2:24][CH2:25][C:4]2=[N:3]1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].CCN(CC)CC.Cl>C1COCC1.CN(C=O)C>[O:26]=[S:2]1(=[O:1])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([C:16]4[O:17][C:27](=[O:28])[NH:19][N:18]=4)[CH:20]=[CH:21][CH:22]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:23][CH2:24][CH2:25][C:4]2=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 69414151HCID 69414151, compound

Product 1

HCID 694140995-{3-[(5,5-Dioxido-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 150 mg (0.40 mmol) of the product obtained in Step B, 85 mg (0.52 mmol) of 1,1′-carbonyldiimidazole and 95 μl (0.68 mmol) of Et3N in a mixture of THF (3.7 ml) and DMF (3.7 ml) is refluxed for 3 hours. The mixture is allowed to return to ambient temperature and is acidified with 1N HCl. A white precipitate forms, which is filtered off to yield the title product.

Workup

  1. temperatureis refluxed for 3 hours
  2. customto return to ambient temperature
  3. filtrationA white precipitate forms, which is filtered off

Sources & evidence

ORD record
ord-4f02414a863d426badd440ab114f4221
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

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