Ammonium Chloride → HCID 178485579, compound

HRID 646671Notes

Reaction equation

HRID 646671 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH3:19])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=2)=[CH:6][N:7]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH3:19])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[NH:22][N:21]=[N:20][N:15]=3)[CH:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 68650324HCID 68650324, compound

Product 1

HCID 178485579HCID 178485579, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 3-amino-6-(3-cyanophenyl)-N-methylpyrazine-2-carboxamide (93 mg, 0.37 mmol) in dry N,N-dimethylformamide (1 mL) were added sodium azide (27 mg, 0.41 mmol), and ammonium chloride (22 mg, 0.41 mmol). The reaction was heated to 100-110° C. overnight. Reaction cooled to room temperature and treated with saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was washed with ethyl acetate (2×30 mL). The sodium bicarbonate layer was cooled to 0° C. and neutralized with 2.0 N hydrochloric acid until the pH of the solution became in the 2-3 range. The aqueous layer was extracted with ethyl acetate (100 mL) and washed with water (20 mL) and saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered, and concentrated at reduced pressure to afford 3-amino-N-methyl-6-[3-(1H-tetrazol-5-yl)phenyl]pyrazine-2-carboxamide (25 mg, 23% yield) as light yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.92 (s, 1H), 8.84 (m, 1H), 8.70 (br s, 1H), 8.40 (br d, 1H), 8.12 (br d, 1H), 7.70 (t, 1H), 2.92 (br s, 3H); MS (EI) for C13H12N8O: 297 (MH+).

Workup

  1. customReaction
  2. temperaturecooled to room temperature
  3. washThe aqueous layer was washed with ethyl acetate (2×30 mL)
  4. temperatureThe sodium bicarbonate layer was cooled to 0° C. and neutralized with 2.0 N hydrochloric acid until the pH of the solution
  5. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
  6. washwashed with water (20 mL) and saturated aqueous sodium chloride (30 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-7679586a696a45a2b19ae26f3c1df6a8
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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