Ammonium Chloride → HCID 178521659, compound
Reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][C:23]([C:27]#[N:28])=[CH:22][C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4].[N-:31]=[N+:32]=[N-:33].[Na+].[NH4+].[Cl-]>CN(C=O)C>[F:30][C:2]([F:29])([F:1])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][C:23]([C:27]4[NH:33][N:32]=[N:31][N:28]=4)=[CH:22][C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
To a solution of Compound 5e (0.232 g, 0.56 mmol) in DMF (5 mL) were added NaN3 (0.11 g, 1.69 mmol) and NH4Cl (0.09 g, 1.68 mmol). The reaction mixture was heated at 120° C. for 14 h, and then cooled to room temperature. An insoluble material was collected by filtration and washed with DMF (5 mL). The filtrate was acidified with 2N HCl (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with H2O (10 mL), dried (MgSO4), and concentrated to give the title compound 5f which was used for subsequent reactions without further purification. MS m/z (MH+) 453.9.
Workup
- temperaturecooled to room temperature
- filtrationAn insoluble material was collected by filtration
- washwashed with DMF (5 mL)
- extractionextracted with EtOAc (3×10 mL)
- washThe combined organic layers were washed with H2O (10 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3189bd5f9442443ba6607e4c02269a7c
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553850B2
Reaction notes
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