Sodium Azide → HCID 18932816, compound

HRID 1597949Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=2)[CH2:17][CH2:16]1.N([O-])=O.[Na+].[N-:29]=[N+:30]=[N-].[Na+]>C(O)(=O)C.O>[N:24]([C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][CH2:16][N:15]2[C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)=[CH:19][CH:20]=1)=[N+:29]=[N-:30]

Participants

Conditions

Temperature: 22 °C

Procedure

To 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-6-ylamine (104 mg, 0.323 mmol; from Example 30) in 80% acetic acid/H2O (8 mL) was added NaNO2 (35 mg, 0.35 mmol) in H2O(200 μL) at 5° C. After stirring 10 min. at 5° C. a solution of NaN3 (22mg, 0.34 mmol) in H2O(200 μL) was added and the mixture was allowed to warm to 22° C. and stirred for 1 hour. Following the removal of solvents by lyophilization the residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3 (2×), and brine, and the organic phase was dried over MgSO4(s), filtered and concentrated in vacuo. The residue was chromatographed on silica (2% MeOH/CHCl3) to afford 72 mg of the azide. (M.P. 184°-186° C. (dec); LC-MS: 349 (MH+); anal. RP18-HPLC RT: 4.70 min.).

Workup

additionwas added
customthe removal of solvents by lyophilization the residue
dissolutionwas dissolved in EtOAc
washwashed with saturated aqueous NaHCO3 (2×), and brine
dry with materialthe organic phase was dried over MgSO4(s)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica (2% MeOH/CHCl3)

Sources & evidence

ORD record: ord-af80e8bd3a514d14820cc0393b42cb7f
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05736534

Reaction notes

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