HCID 71253907, compound → HCID 71254141, compound

HRID 1775065Notes

Reaction equation

HRID 1775065 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[N:9](C3CCCCO3)[N:8]=2)[C:3]1=[O:28]>Cl.O1CCOCC1>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[NH:9][N:8]=2)[C:3]1=[O:28]

Participants

4

Reactant 1

HCID 71253907HCID 71253907, compound

Product 1

HCID 71254141HCID 71254141, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1-methyl-3-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one (0.140 g, 0.371 mmol) in 4.00 M of Hydrogen chloride in 1,4-Dioxane (3.00 mL) and 1,4-Dioxane (3.00 mL, 38.4 mmol) was stirred at RT for 18 h. The reaction was concentrated. The crude product was submitted HPLC to give 254 (16.9 mg, 15.4% yield). ESI MS m/z=295.1 (M+1). 1H NMR (400 MHz, DMSO) δ 9.18 (s, 1H), 9.04 (s, 1H), 8.82 (s, 1H), 8.56 (d, J=4.3 Hz, 1H), 8.32 (d, J=8.0 Hz, 1H), 7.50 (dd, J=7.9, 4.7 Hz, 1H), 4.01-3.93 (m, 2H), 3.64-3.53 (m, 2H), 2.86 (s, 3H)

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-a643313648384d91962bcbc14097cb2d
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…