Ammonium Chloride → HCID 178425832, compound

HRID 883034Notes

Reaction equation

HRID 883034 reaction equation
[C:1]([C:3]1[C:4]([NH:9][C:10]2[CH:11]=[C:12]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[CH:17]=2)=[O:14])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH:29]1[C:1]([C:3]2[C:4]([NH:9][C:10]3[CH:11]=[C:12]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[CH:17]=3)=[O:14])=[N:5][CH:6]=[CH:7][CH:8]=2)=[N:2][N:31]=[N:30]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 691651193-(3-cyanopyridin-2-ylamino)-N-(3-isopropylphenyl)-4-methylbenzamide

Product 1

HCID 178425832HCID 178425832, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To 3-(3-cyanopyridin-2-ylamino)-N-(3-isopropylphenyl)-4-methylbenzamide (11 mg, 0.03 mmol), sodium azide (21 mg, 0.30 mmol) and ammonium chloride (17 mg, 0.30 mmol) was added DMF (0.5 mL). The mixture was heated to 130° C. in the microwave for 10 minutes. The reaction was quenched with saturated sodium bicarbonate and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to yield 3-(3-(1H-tetrazol-5-yl)pyridin-2-ylamino)-N-(3-isopropylphenyl)-4-methylbenzamide. MS m/z [M+H]+=414; Calc'd for C23H23N7O: 413.49.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3fd550d3aed34aab82f71fb066a8c665
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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