Hydrochloric Acid → 2-(Pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802238Notes

Reaction equation

HRID 1802238 reaction equation
[N:1]1([C:6]2[N:22]=[C:9]3[CH:10]=[C:11]([NH:14]C(=O)OC(C)(C)C)[CH:12]=[CH:13][N:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>ClCCl>[N:1]1([C:6]2[N:22]=[C:9]3[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][N:8]3[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67774330HCID 67774330, compound

Product 1

HCID 677741812-(Pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (340 mg, 1.12 mmol) and hydrochloric acid (5N in ether, 25 ml, 125 mmol) in dichloromethane (10 ml) was stirred for 20 hours at 25° C. The solvent was evaporated, the residue was triturated with sat. sodium hydrogencarbonate solution, the solid was filtered off, washed with water several times and dried affording 2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (194 mg, 85.2%) as a light yellow solid. mp: 221-225° C., MS: m/z=204.4 (M+H+)

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with sat. sodium hydrogencarbonate solution
  3. filtrationthe solid was filtered off
  4. washwashed with water several times
  5. customdried

Sources & evidence

ORD record
ord-709ea05a492e45b59743b17051f46355
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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