Hydrochloric Acid → HCID 178490721, compound

HRID 1660792Notes

Reaction equation

HRID 1660792 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][CH2:18][N:17]([S:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=4[O:31][CH3:32])(=[O:23])=[O:22])[C:16]=3[CH:33]=2)=[O:11])=[CH:5][CH:4]=1)#[N:2].[Cl-].[NH4+].[N-:36]=[N+:37]=[N-:38].[Na+].Cl>CN(C)C=O>[NH:36]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]3[CH:13]=[CH:14][C:15]4[O:20][CH2:19][CH2:18][N:17]([S:21]([C:24]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=5[O:31][CH3:32])(=[O:23])=[O:22])[C:16]=4[CH:33]=3)=[O:11])=[CH:7][CH:8]=2)=[N:2][N:38]=[N:37]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 667886204-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (4-cyano-phenyl)-amide

Product 1

HCID 178490721HCID 178490721, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A microwave tube was charged with a solution of 4-(5-chloro-2-methoxybenzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (4-cyano-phenyl)-amide (50 mg, 0.10 mmol) in dimethylformamide (2.0 mL). Ammonium chloride (102 mg, 1.9 mmol) and sodium azide (121 mg, 1.9 mmol) were added and the tube was sealed under an argon atmosphere and irradiated in a microwave oven at a temperature of 155° C. for 35 min. The mixture was then acidified with HCl 1N and extracted three times with ethyl acetate. The combined organic extracts were dried over sodium sulfate and evaporated. The crude was resuspended in dichloromethane and sonicated. Filtration yielded 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide as a white solid, 35 mg (64%), MS (ISP): m/e=525.0, 527.0 (M−H).

Workup

  1. customthe tube was sealed under an argon atmosphere
  2. customirradiated in a microwave oven at a temperature of 155° C. for 35 min
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. customevaporated
  6. customsonicated
  7. filtrationFiltration

Sources & evidence

ORD record
ord-cecd7e35f90447a7a636ebf626c59d4f
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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