Hydrochloric Acid → HCID 86640699, compound

HRID 336799Notes

Reaction equation

HRID 336799 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([NH:12]C2C(NC3C=C(OC)C=C(OC)C=3)=NC3C(=CC=CC=3)N=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[N:34]1[NH:35][N:36]=[N:2][C:1]=1[C:3]1[CH:4]=[C:5]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 16045463HCID 16045463, compound

Product 1

HCID 86640699HCID 86640699, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-cyano-N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide (0.20 g, 0.44 mmol), prepared using procedures similar to those described in Example 115, in dimethylformamide (1.2 mL) at 50° C. were added sodium azide (0.11 g, 1.76 mmol) and ammonium chloride (94 mg, 1.76 mmol). The crude mixture was heated at 100° C. overnight. The reaction was cooled to room temperature treated with ice water (20 mL) followed by concentrated hydrochloric acid (10 mL). The solid obtained was filtered under reduced pressure and washed with hexane (20 mL), diethyl ether (20 mL), and ethyl acetate (5 mL) to afford N-(3-{[3,5-bis(methoxy)phenyl]amino}) quinoxalin-2-yl)-3-(2H-tetrazol-5-yl)benzenesulfonamide (55 mg, 25%) as light yellow solid. MS (EI) m/z for C23H20N8O4S: 505.0 (MH+).

Workup

  1. customThe solid obtained
  2. filtrationwas filtered under reduced pressure
  3. washwashed with hexane (20 mL), diethyl ether (20 mL), and ethyl acetate (5 mL)

Sources & evidence

ORD record
ord-0df995aca8a4422b9c064aa55ac4f07b
Source dataset
uspto-grants-2014_11
Patent number
US08889664B2

Reaction notes

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