Hydrochloric Acid → HCID 57448670, compound

HRID 237361Notes

Reaction equation

HRID 237361 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([NH:12][C:13]2[C:22]([NH:23][C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[CH:25]=3)=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=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>[CH3:31][O:30][C:28]1[CH:29]=[C:24]([NH:23][C:22]2[C:13]([NH:12][S:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]4[N:34]=[N:35][NH:36][N:2]=4)[CH:4]=3)(=[O:10])=[O:11])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:25]=[C:26]([O:32][CH3:33])[CH:27]=1

Participants

6

Reactant 4

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

Product 1

HCID 57448670HCID 57448670, compoundYield 25%

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) 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(methyloxy)phenyl]amino}quinoxalin-2-yl)-3-(2H-tetrazol-5-yl)benzenesulfonamide (55 mg, 25%) as light yellow solid. MS (EI) 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-80a363142c204bf29b2cb42b91cacd30
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Reaction notes

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