Ammonium Chloride → HCID 178432381, compound

HRID 1868468Notes

Reaction equation

HRID 1868468 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[N:10]=[C:9]([CH3:11])[C:8]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:7]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[N:6]2[CH:29]=1)#[N:2].[N-:30]=[N+:31]=[N-:32].[Na+].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:7]1[N:6]2[CH:29]=[C:3]([C:1]3[NH:32][N:31]=[N:30][N:2]=3)[N:4]=[C:5]2[N:10]=[C:9]([CH3:11])[C:8]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 70323530HCID 70323530, compound

Product 1

HCID 178432381HCID 178432381, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of tert-butyl (2-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (intermediate for Example 152, 27 mg, 0.06 mmol) in DMF (2 mL) was added NaN3 (6 mg, 0.09 mmol) and NH4Cl (5 mg, 0.09 mmol). After heating to 100° C. for 24 h, the reaction was diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded crude tert-butyl (5-(2,4-dichlorophenyl)-7-methyl-2-(1H-tetrazol-5-yl)imidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (20 mg).

Workup

  1. washThe organic layer was washed with satd aq NH4Cl and brine
  2. dry with materialto drying over MgSO4
  3. filtrationFiltration, concentration
  4. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-cbb027a88c39414d82cd3c7241f40b76
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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