Hydrogen chloride-ethyl acetate → HCID 69671373, compound

HRID 1497570Notes

Reaction equation

HRID 1497570 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH3:31])=[N:22][N:23]=3)[CH:20]=2)[CH:12]=[CH:13][CH:14]=1)=O)(C)(C)C.[ClH:32].C(OCC)(=O)C>>[ClH:32].[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH3:31])=[N:22][N:23]=3)[CH:20]=2)[CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69671140HCID 69671140, compound

Product 1

HCID 69671373HCID 69671373, compoundYield 15%

Procedure

A mixture of 6-(3-(tert-butoxycarbonylamino)phenyl)-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (78 mg, 0.19 mmol) in HCl/ethyl acetate (2M, 20 mL) was stirred at room temperature for about 3 h. The mixture was concentrated under reduced pressure to give the crude compound. It was recrystallized in MeOH/ethyl acetate to give the title compound (9.8 mg, 15% yield) as yellow solids. 1H NMR (DMSO-d6): 8.36 (s, 1H), 8.16 (d, J=8.1 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.78-7.60 (m, 5H), 7.49 (d, J=6.9 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.23 (t, J=6.6 Hz, 1H), 3.92 (s, 3H). MS: m/z 317.2 [M+H+].

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give the crude compound
  3. customIt was recrystallized in MeOH/ethyl acetate

Sources & evidence

ORD record
ord-4460c05976b4455c901aad782e187b4d
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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