Hydrochloric Acid → HCID 86664057, compound

HRID 712349Notes

Reaction equation

HRID 712349 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:20]=[C:19]([CH3:21])[O:18][N:17]=3)=[CH:14][C:13]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][C:31]([CH3:39])([C:34]([O:36]CC)=[O:35])[CH2:30][CH2:29]4)=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[OH-].[Na+].Cl>CCO>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:20]=[C:19]([CH3:21])[O:18][N:17]=3)=[CH:14][C:13]([C:22]3[CH:27]=[N:26][C:25]([N:28]4[CH2:29][CH2:30][C:31]([CH3:39])([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]4)=[N:24][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86664056HCID 86664056, compound

Product 1

HCID 86664057HCID 86664057, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (192 mg, 0.349 mmol) was dissolved in EtOH (20 mL) and 2M aqueous NaOH (10 mL) added. The reaction mixture was stirred at 70° C. for 2 h then cooled to rt and 2M HCl (20 mL) added. The mixture was extracted with hot EtOAc (3×50 mL), the aqueous phase saturated with NaCl and further extracted with EtOAc (50 mL) and the combined organic fractions washed with brine, separated, dried (Na2SO4) and concentrated under reduced pressure. The solid residue was washed with MeCN then Et2O to afford Compound 213 (163 mg, 89%) as a pale-yellow solid. 1H NMR (DMSO-d6): δ10.98 (bs, 1H), 8.81 (s, 2H), 8.11 (d, J=1.8 Hz, 1H), 8.10 (d, J=1.8 Hz, 1H), 7.06 (bt, J=5.4 Hz, 1H), 4.31 (dt, J=13.9 and 4.4 Hz, 2H), 3.37 (ddd, J=13.3, 10.2 and 2.9 Hz, 2H), 3.26-3.19 (m, 2H), 2.76 (s, 3H), 2.09-2.02 (m, 2H), 1.43 (ddd, J=13.8, 10.2 and 3.9 Hz, 2H), 1.21 (s, 3H), 1.13 (t, J=7.2 Hz, 3H). MS: 523.13 [M+H]+.

Workup

  1. temperaturethen cooled to rt
  2. extractionThe mixture was extracted with hot EtOAc (3×50 mL)
  3. extractionthe aqueous phase saturated with NaCl and further extracted with EtOAc (50 mL)
  4. washthe combined organic fractions washed with brine
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. washThe solid residue was washed with MeCN

Sources & evidence

ORD record
ord-22cc60084fb248f695513a2dd1ef3d51
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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