Hydrochloric Acid → HCID 178423424, compound

HRID 388148Notes

Reaction equation

HRID 388148 reaction equation
[CH3:1]C1C=C(C2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)C=CC=1C1N=CNN=1.C[C:31]1[CH:32]=[C:33]([C:48]2[N:53]=[C:52]3[N:54]([CH2:58][CH2:59][CH:60]4[CH2:65][CH2:64][O:63][CH2:62][CH2:61]4)[C:55](=[O:57])[NH:56][C:51]3=[N:50][CH:49]=2)[CH:34]=[CH:35][C:36]=1[C:37]1[N:41]=[CH:40][N:39](C2CCCCO2)[N:38]=1.Cl>O1CCOCC1>[CH3:1][C:32]1[CH:31]=[C:36]([C:37]2[N:41]=[CH:40][NH:39][N:38]=2)[CH:35]=[CH:34][C:33]=1[C:48]1[N:53]=[C:52]2[N:54]([CH2:58][CH2:59][CH:60]3[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)[C:55](=[O:57])[NH:56][C:51]2=[N:50][CH:49]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66699807HCID 66699807, compoundHCID 178422914HCID 178422914, compound

Product 1

HCID 178423424HCID 178423424, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

6-(3-Methyl-4-(1H-1,2,4-Triazol-3-yl)phenyl)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one. 6-(3-Methyl-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-1-((tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one (0.283 g, 0.578 mmol) was added to 6.0 M hydrogen chloride in dioxane (4.0 mL) and stirred at 25° C. for 2 h. The solution was condensed under reduced pressure and purified using reverse-phase semi-preparatory HPLC (20-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Clean fractions were combined, neutralized with ammonium hydroxide, concentrated, diluted with water (20 mL). The desired product was collected by filtration to afford the title compound as an off white solid, 99.5% pure, (0.061 g, 26%). 1H NMR (400 MHz, CD3OD-d4) δ 8.40 (br. s., 1H), 8.07 (s, 1H), 8.00 (s, 1H), 7.94 (d, J=8.20, 1H), 7.55 (d, J=8.20, 1H), 4.04 (t, J=7.22, 2H), 3.90 (dd, J=11.32, 3.51, 2H), 3.34-3.42 (m, 3H), 2.49 (s, 3H), 1.70-1.87 (m, 4H), 1.58 (dddd, J=10.93, 7.32, 4.10, 3.81, 1H), 1.50-1.66 (m, 1H), 1.22-1.40 (m, 2H); MS (ESI) m/z 408.5[M+1]+; mp 258-260° C.

Workup

  1. customcondensed under reduced pressure
  2. custompurified
  3. customreverse-phase semi-preparatory HPLC (20-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  4. concentrationconcentrated
  5. additiondiluted with water (20 mL)
  6. filtrationThe desired product was collected by filtration

Sources & evidence

ORD record
ord-54ae2490d05c47948cd7d930c49b90df
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

Loading…