Hydrogen chloride-ethyl acetate → (6r)-n-Cyclobutyl-6-(methoxymethyl)-n-methyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine hydrochloride

HRID 1877901Notes

Reaction equation

C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH:21]3[CH2:24][CH2:23][CH2:22]3)[CH3:20])=[N:18][C:12]=2[O:11][C@@H:10]([CH2:25][O:26][CH3:27])[CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:34]>CO.[OH-].[OH-].[Pd+2]>[ClH:34].[CH:21]1([N:19]([CH3:20])[C:17]2[CH:16]=[N:15][C:13]3[CH2:14][NH:8][CH2:9][C@H:10]([CH2:25][O:26][CH3:27])[O:11][C:12]=3[N:18]=2)[CH2:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (6R)-8-benzyl-N-cyclobutyl-6-(methoxymethyl)-N-methyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine (390 mg) in methanol (10 mL) was added 20% Pd(OH)2/C (50 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 6 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. To a solution of the obtained crude product in ethyl acetate (10 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (291 μL), and the mixture was stirred for 5.5 hr. The reaction mixture was filtered, and the obtained crystals were washed with ethyl acetate to give the title compound (206 mg, 62%).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customTo a solution of the obtained crude product in ethyl acetate (10 mL)
stirringthe mixture was stirred for 5.5 hr
filtrationThe reaction mixture was filtered
washthe obtained crystals were washed with ethyl acetate

Sources & evidence

ORD record: ord-218e987078294c7e8f426a535afe3777
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314088B2

Reaction notes

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