Hydrochloric Acid → 6-(3,4-difluorophenyl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

HRID 1476650Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[S:17][C:16]3[C:15](=[O:18])[N:14]([CH:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)[C:13](=[O:32])[N:12]([CH2:33][C:34]4[O:38][N:37]=[C:36]([CH2:39][CH3:40])[N:35]=4)[C:11]=3[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:41]>O1CCOCC1>[ClH:41].[F:1][C:2]1[CH:3]=[C:4]([C:9]2[S:17][C:16]3[C:15](=[O:18])[N:14]([CH:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]4)[C:13](=[O:32])[N:12]([CH2:33][C:34]4[O:38][N:37]=[C:36]([CH2:39][CH3:40])[N:35]=4)[C:11]=3[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl 4-[6-(3,4-difluorophenyl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (400 mg, compound B67) in 1,4-dioxane (7 ml) is added a solution of hydrogen chloride in 1,4-dioxane (1.7 ml, 4.0 M). The reaction mixture is stirred for 3 h at 50° C. and subsequently for 12 h at RT. In order to complete the reaction an additional amount of a solution of hydrogen chloride in 1,4-dioxane (0.9 ml, 4.0 M) is added and the reaction mixture is stirred for 1 h at 65° C. Afterwards all volatiles are removed under reduced pressure to afford the title compound as a solid.

Workup

additionis added
stirringthe reaction mixture is stirred for 1 h at 65° C
customAfterwards all volatiles are removed under reduced pressure

Sources & evidence

ORD record: ord-be3422d17663456eaf21a9276d0f4b05
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018175B2

Reaction notes

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