1,4-Dioxane hydrochloride → (2R)-N-cyclopropyl-N-{(1R)-1-[1-(3-methoxypropyl)-3-methyl-1H-indazol-6-yl]ethyl}morpholine-2-carboxamide hydrochloride

HRID 922413Notes

Reaction equation

HRID 922413 reaction equation
[CH:1]1([N:4]([C@@H:20]([C:22]2[CH:30]=[C:29]3[C:25]([C:26]([CH3:36])=[N:27][N:28]3[CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:24][CH:23]=2)[CH3:21])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.[ClH:37].O1CCOCC1>C(Cl)(Cl)Cl>[ClH:37].[CH:1]1([N:4]([C@@H:20]([C:22]2[CH:30]=[C:29]3[C:25]([C:26]([CH3:36])=[N:27][N:28]3[CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:24][CH:23]=2)[CH3:21])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68308651HCID 68308651, compound

Product 1

HCID 86707855(2R)-N-cyclopropyl-N-{(1R)-1-[1-(3-methoxypropyl)-3-methyl-1H-indazol-6-yl]ethyl}morpholine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl (2R)-2-[(cyclopropyl{(1R)-1-[1-(3-methoxypropyl)-3-methyl-1H-indazol-6-yl]ethyl}amino)carbonyl]morpholine-4-carboxylate (44.4 mg) in chloroform (2.0 mL) was added 4-normal hydrogen chloride-dioxane solution (0.75 mL) under ice-cooling, and the mixture was stirred at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in water (1 mL), and then washed with diethyl ether. The aqueous layer was freeze-dried to give (2R)-N-cyclopropyl-N-{(1R)-1-[1-(3-methoxypropyl)-3-methyl-1H-indazol-6-yl]ethyl}morpholine-2-carboxamide hydrochloride [Ex(3-1)] (25 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in water (1 mL)
  4. washwashed with diethyl ether
  5. customThe aqueous layer was freeze-dried

Sources & evidence

ORD record
ord-417c31e79b1d4b73a77f468eba88e839
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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