Hydrochloric Acid → HCID 178518581, compound

HRID 604371Notes

Reaction equation

HRID 604371 reaction equation
[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[CH:5][C:4]=2[NH:3]1.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[NH:17]1[C:15]([C:6]2[CH:7]=[CH:8][C:9]3[C:10]4[S:14][CH:13]=[CH:12][C:11]=4[C:2](=[O:1])[NH:3][C:4]=3[CH:5]=2)=[N:16][N:19]=[N:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 50941660HCID 50941660, compound

Product 1

HCID 178518581HCID 178518581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile (1.0 eq, 20 mg, 0.088 mmol) was dissolved in anhydrous DMF (0.15 ml). Sodium azide (4.0 eq, 23 mg, 0.354 mmol) and ammonium chloride (4.0 eq, 19 mg, 0.354 mmol) were added and the mixture stirred at 120° C. overnight. The reaction mixture was cooled down and water was added. Addition of aqueous 6 N HCl induced formation of a precipitate. After filtration and drying in vacuo, 7-(1H-tetrazol-5-yl)thieno[3,2-c]quinolin-4(5H)-one was isolated as a greenish solid (18 mg, 76% yield)). LCMS (ES): 95% pure, m/z 270 [M+1]+, 242 [M+1-N2]+; 1H NMR (DMSO-d6, 400 MHz) δ 7.64 (d, J=5.2, 1H), 7.86 (dd, J=1.6, J=8.4, 1H), 7.89 (d, J=5.2, 1H), 8.09 (d, J=8.0, 1H), 8.16 (d, J=1.6, 1H), 12.03 (s, 1H) ppm.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. filtrationAfter filtration
  3. customdrying in vacuo

Sources & evidence

ORD record
ord-3be46877810c4ba49f75fa07486c0033
Source dataset
uspto-grants-2011_03
Patent number
US07910600B2

Reaction notes

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