Ammonium Chloride → HCID 178466538, compound

HRID 1833259Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

The mixture of 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (50 mg, 140 mmol), sodium azide (20 mg, 310 mmol) and ammonium chloride (16.2 mg, 310 mmol) in DMF (2 mL) was stirred at 120° C. for 24 h. After removal of solvent, the crude product was purified directly by HPLC (Reverse C18, 10%-90% acetonitrile in water in 10 min) afforded our desired product [6,7-Dimethoxy-4-(1H-tetrazol-5-yl)-isoquinolin-1-yl]-(3-ethoxy-phenyl)-methanone with trifluoro-acetic (31 mg, 55%) as a light yellow solid. LC/MS m/e calcd for C21H19N5O4 (MH+) 406, found 406.

Workup

customAfter removal of solvent
customthe crude product was purified directly by HPLC (Reverse C18, 10%-90% acetonitrile in water in 10 min)

Sources & evidence

ORD record: ord-eed70cc3c1734665aa63b5776de29804
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067529B2

Reaction notes

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