Hydrochloric Acid → HCID 67520354, compound

HRID 1926342Notes

Reaction equation

HRID 1926342 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:31])=[N:12][CH:13]=[C:14]([C:16]2[CH:17]=[N:18][N:19]([CH:21]3[CH2:30][CH2:29][C:24]4(OCC[O:25]4)[CH2:23][CH2:22]3)[CH:20]=2)[CH:15]=1.Cl>O1CCOCC1>[NH2:31][C:11]1[N:12]=[CH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([CH:21]3[CH2:22][CH2:23][C:24](=[O:25])[CH2:29][CH2:30]3)[CH:20]=2)=[CH:15][C:10]=1[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67521206HCID 67521206, compound

Product 1

HCID 67520354HCID 67520354, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-benzothiazol-2-yl-5-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-4-yl]-pyridin-2-ylamine (0.750 g, 1.7 mmol) in dioxane (5 mL) was added 2 N HCl (1 mL), and the solution was stirred at RT for 1 h. The solvents were evaporated, and aq. satd. NaHCO3 solution (30 mL) was added to the residue. The mixture was extracted with CH2Cl2 (3×40 mL), and the combined extracts were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel using EtOAc/Hexanes (1:1) to give the title compound as yellow solid. 1H NMR (400 MHz, CDCl3): δ=8.33 (d, J=2.2 Hz, 1H), 8.02 (dd, J=8.4, 0.4 Hz, 1H), 8.01 (d, J=2.4 Hz, 1H), 7.91 (ddd, J=8.4, 1.2, 0.4 Hz, 1H), 7.79 (d, J=0.6 Hz, 1H), 7.71 (d, J=0.6 Hz, 1H), 7.51 (ddd, J=8.4, 7.4, 1.2 Hz, 1H), 7.41 (ddd, J=8.0, 7.4, 1.4 Hz, 1H), 7.14 (brs, 2H), 4.72-4.64 (mc, 1H), 2.70-2.47 (m, 6H), 2.46-2.34 (m, 2H). MS(ES+): m/z=390.14 (100) [MH+]. HPLC: tR=3.13 min (polar—5 min, ZQ3).

Workup

  1. customThe solvents were evaporated
  2. additionNaHCO3 solution (30 mL) was added to the residue
  3. extractionThe mixture was extracted with CH2Cl2 (3×40 mL)
  4. washthe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-16d79eec7b53410aa7f7c13b143ac874
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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