Hydrochloric Acid → 5-[(3-Chlorophenyl)methoxy]-3-(1-piperazinyl)-2-pyrazinamine

HRID 2182152Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([NH2:20])=[N:18][CH:17]=[C:16]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Cl:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][O:21][C:16]1[N:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:19]([NH2:20])=[N:18][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

3′-Amino-6′-(3-chloro-benzyloxy)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-3s (150 mg, 357 μmol) was dissolved in 1,4-dioxane (6 mL) and an HCl solution (0.90 mL, 4 M in 1,4-dioxane, 3.6 mmol) was added with stirring at 40° C. The solution was stirred at 40° C. for 18 h and concentrated in vacuo to approximately 2 mL. The mixture was diluted with Et2O. The resulting brown solid was collected by filtration and washed twice with Et2O. The solid was purified by preparative HPLC to give the title compound 3-P as a tan solid (19 mg, 17% yield).

Workup

stirringThe solution was stirred at 40° C. for 18 h
concentrationconcentrated in vacuo to approximately 2 mL
additionThe mixture was diluted with Et2O
filtrationThe resulting brown solid was collected by filtration
washwashed twice with Et2O
customThe solid was purified by preparative HPLC

Sources & evidence

ORD record: ord-c812a46b5bf5470d9f8ce90c22d6b8f8
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894050B2

Reaction notes

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