Hydrochloric Acid → Piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide hydrochloride

HRID 550810Notes

Reaction equation

[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:28])[NH:16][C:17]2[S:18][C:19]3[N:20]=[CH:21][N:22]=[C:23]([O:26][CH3:27])[C:24]=3[N:25]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>C(Cl)Cl>[ClH:1].[CH3:27][O:26][C:23]1[C:24]2[N:25]=[C:17]([NH:16][C:15]([N:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)=[O:28])[S:18][C:19]=2[N:20]=[CH:21][N:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Hydrogen chloride gas was bubbled through a solution of 4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester (5.20 g, 13 mmol) in methylene chloride (70 mL) for 10 min at 0° C. A white precipitate formed. The resulting slurry was stirred at 25° C. for 2 h. At this time, the mixture was concentrated in vacuo and dried under high vacuum to afford piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide hydrochloride (4.61 g) as a white solid; LRMS for C11H14N6O2S (M+H)+ at m/z=295. This solid was used in the next step without further purification.

Workup

customA white precipitate formed
concentrationAt this time, the mixture was concentrated in vacuo
customdried under high vacuum

Sources & evidence

ORD record: ord-ff6a7e27a8fb403d85a3024830d7eaee
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947692B2

Reaction notes

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