Hydrochloric Acid → HCID 10468897, compound
Reaction equation
Cl.[NH2:2][C:3]1[C:4]([Cl:19])=[N:5][CH:6]=[CH:7][C:8]=1[NH:9][CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[F:18].[N:20]([O-])=O.[Na+].[OH-].[NH4+]>C(O)C>[Cl:19][C:4]1[C:3]2[N:2]=[N:20][N:9]([CH2:10][C:11]3[C:12]([F:18])=[CH:13][CH:14]=[CH:15][C:16]=3[F:17])[C:8]=2[CH:7]=[CH:6][N:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A 3-L flask equipped with a thermometer and mechanical stirrer was charged with concentrated hydrochloric acid (140 mL), 1N hydrochloric acid (380 mL) and absolute ethanol (1.10L) and cooled to 5° C. in an ice bath. 3-Amino-2-chloro-4-[(2,6-difluorobenzyl) amino]pyridine(40 g, 0.15mol)(from example 1B) was added followed by the addition of sodium nitrite(13.3 g, 0.19 mol). The solution was stirred for 35 minutes at 5° C., ammonium hydroxide was added to pH9, and the solution extracted with chloroform (2×1.00L). The combined organic extracts were dried (sodium sulphate) and concentrated to produce 4-chloro-1-(2,6-difluorobenzyl)-1H-1,2,3- triazolo[4,5-c]pyridine as a damp pink solid in quantitative yield, sufficiently pure for further reaction. A sample was purified by flash column chromatography to give the analytical sample, mp.=133°-139° C. 1H NMR (DMSO-d6): 6.10 (s, 2H, CH2), 7.10-7.65(m, 3H, C-3'H, C-4'H, C-5'H), 7.95 (d, J=5.9 Hz, 1H, C-7H), 8.43 (d, J=5.9 Hz, 1H, C-6H).
Workup
- customA 3-L flask equipped with a thermometer and mechanical stirrer
- extractionthe solution extracted with chloroform (2×1.00L)
- dry with materialThe combined organic extracts were dried (sodium sulphate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fc606bb63521450794eb4c300b1a4765
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166209
Reaction notes
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