Hydrochloric Acid → HCID 58857728, compound

HRID 2353055Notes

Reaction equation

HRID 2353055 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH3:31])[CH:25]=4)=[CH:22][N:23]=3)[N:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C1COCC1.Cl.CCN(CC)CC>O1CCOCC1.O>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C:21]2[N:19]3[N:20]=[C:15]([NH:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:16]=[CH:17][C:18]3=[N:23][CH:22]=2)[CH:29]=[CH:28][N:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 58857804HCID 58857804, compound

Product 1

HCID 58857728HCID 58857728, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

280 mg (0.66 mmol) of 4-[3-(2-methoxypyridin-4-yl)imidazo[1,2-b]pyridazin-6-ylamino]piperidine-1-carboxylic acid tert-butyl ester were introduced into 3 ml of THF and, after addition of 0.8 ml of HCl in dioxane (4M), stirred at RT overnight. HCl (conc.) was added, and the mixture was heated at 70° C. for 4 hours. The reaction was diluted with water, adjusted to pH 11 with Et3N and extracted three times with ethyl acetate. The combined organic phases were filtered through a silicone filter (from Whatman) and concentrated. In the final fractionation by chromatography on silica gel, 92 mg of the desired product were isolated.

Workup

  1. temperaturethe mixture was heated at 70° C. for 4 hours
  2. extractionextracted three times with ethyl acetate
  3. filtrationThe combined organic phases were filtered through a silicone
  4. filtrationfilter (from Whatman)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8dd899ce448c4364af53be27f2972a14
Source dataset
uspto-grants-2010_07
Patent number
US07750000B2

Reaction notes

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