Hydrochloric Acid → (S)-1-(5-fluoropyrimidin-2-yl)-6-methyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine-hydrochloride salt

HRID 2177636Notes

Reaction equation

HRID 2177636 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[CH2:15][C@H:14]([CH3:17])[N:13](C(OC(C)(C)C)=O)[CH2:12][C:11]=3[N:10]=[N:9]2)=[N:6][CH:7]=1.[ClH:25].O1CCOCC1>C(Cl)Cl>[ClH:25].[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[CH2:15][C@H:14]([CH3:17])[NH:13][CH2:12][C:11]=3[N:10]=[N:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90408514(S)-tert-butyl 1-(5-fluoropyrimidin-2-yl)-6-methyl-6,7-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridine-5(4H)-carboxylate

Product 1

HCID 90408506(S)-1-(5-fluoropyrimidin-2-yl)-6-methyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine-hydrochloride saltYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(5-fluoropyrimidin-2-yl)-6-methyl-6,7-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridine-5(4H)-carboxylate (0.711 g, 2.13 mmol) in CH2Cl2 (10 mL) was added 4M HCl in dioxane (2.66 mL, 10.6 mmol). After stirring overnight at rt, the reaction was concentrated in vacuo to give the desired product as a light yellow solid (0.580 mg, 100%). MS (ESI) mass calcd. C10H11FN6, 234.23. m/z found, 235.1 [M+H]+. 1H NMR (400 MHz, DMSO) δ 9.97-9.69 (m, 1H), 9.15 (s, 2H), 4.58-4.35 (m, 2H), 3.80-3.47 (m, 2H), 3.21-3.03 (m, 1H), 1.46 (d, J=6.5 Hz, 3H).

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-1d20d64d8cf7482e96d73e0263f362c3
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

Loading…