Hydrogen chloride-ethyl acetate → ethyl 5-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate trihydrochloride

HRID 1879397Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][CH2:15]2)=[CH:11][C:10]=1[O:18][CH2:19][C:20]1[N:21]=[CH:22][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:24][CH:25]=1)=O)(C)(C)C.[ClH:31].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:31].[ClH:31].[ClH:31].[NH2:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][CH2:15]2)=[CH:11][C:10]=1[O:18][CH2:19][C:20]1[N:21]=[CH:22][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:24][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

690 mg of ethyl 5-[({6-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]pyrazine-2-carboxylate was dissolved in 7.00 mL of ethyl acetate, and 4.17 mL of a 4 M hydrogen chloride/ethyl acetate solution was added thereto, followed by stirring at 50° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, and the obtained residue was solidified by the addition of isopropanol to obtain 712 mg of ethyl 5-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate trihydrochloride.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
additionthe obtained residue was solidified by the addition of isopropanol

Sources & evidence

ORD record: ord-e22d0fa7fd324cbf90b3942619158e93
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314240B2

Reaction notes

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