Hydrochloric Acid → HCID 53311316, compound

HRID 1854623Notes

Reaction equation

HRID 1854623 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:9][N:10]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([NH:17][C:15]2[N:16]=[C:11]([C:8]3[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=3)[CH:12]=[CH:13][CH:14]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53311315HCID 53311315, compound

Product 1

HCID 53311316HCID 53311316, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of [6-(2-[1,3]dioxolan-2-yl-thiazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (270 mg, 0.793 mmol) in THF (8 mL) was added 2N HCl (2 mL). The mixture was heated at 60° C. overnight. After cooling, saturated NaHCO3 was added to basic pH then the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure to afford the title compound as a yellow solid (220 mg, 94%). 1H NMR (DMSO-d6, 300 MHz): δ=9.94 (s, 1H), 9.83 (s, 1H), 8.87 (s, 1H), 8.12 (d, J=4.9 Hz, 1H), 7.90 (s, 1H), 7.78 (m, 1H), 7.64 (d, J=7.6 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 6.80 (d, J=5.1 Hz, 1H), 2.35 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-793ed9122a25412e85bbd19faa71ac09
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

Loading…