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Hydrochloric Acid → 2-(3-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802262
Notes
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Reaction equation

HRID 1802262 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[N:16]=[C:10]2[CH:9]=1)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([C:15]2[N:16]=[C:10]3[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][N:11]3[N:14]=2)[CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67776674[2-(3-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-carbamic acid tert-butyl ester

Product 1

HCID 677739812-(3-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amineYield 128.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-Dioxane
Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of [2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-carbamic acid tert-butyl ester (5.5 g, 16.2 mmol) in DCM (100 ml) was added a solution of HCl in dioxane (4 N, 20 ml). The resultant reaction mixture was stirred at 25° C. for 16 h. Volatiles were removed in vacuum, and the resultant residue was dried under vacuum to give 2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (5 g, quant) as light yellow solid. LC-MS: m/z=241.0 [M+H]+.

Workup

  1. customThe resultant reaction mixture
  2. customVolatiles were removed in vacuum
  3. dry with materialthe resultant residue was dried under vacuum

Sources & evidence

ORD record
ord-1f0fc59186bd451bb1257d11afdffe58
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349824B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes