Hydrochloric Acid → 7-(Dimethoxymethyl)-6-(piperidin-4-yl)-1,2,3,4-tetrahydro-1,8-naphthyridine hydrochloride

HRID 1778069Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:27][CH3:28])[C:4]1[C:13]([CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1.[ClH:29]>CO>[ClH:29].[CH3:28][O:27][CH:3]([O:2][CH3:1])[C:4]1[N:5]=[C:6]2[C:11]([CH2:10][CH2:9][CH2:8][NH:7]2)=[CH:12][C:13]=1[CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl 4-(2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)piperidine-1-carboxylate (Intermediate 339, 1.0 g, 2.20 mmol) and 3M HCl in MeOH (7 ml) was stirred at 60° C. After stirring for 13 h, the reaction mixture was cooled to room temperature and evaporated. The residue was diluted with MeOH and evaporated again (4×). The title compound was obtained as a brown solid. (UPLC-MS 3) tR 0.31 min; ESI-MS 292.2 [M+H]+.

Workup

stirringAfter stirring for 13 h
temperaturethe reaction mixture was cooled to room temperature
customevaporated
additionThe residue was diluted with MeOH
customevaporated again (4×)

Sources & evidence

ORD record: ord-7a621c1ab2704abfa330eb72097848bd
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266883B2

Reaction notes

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