HCID 86682478, compound → HCID 141465658, compound

HRID 408645Notes

Reaction equation

C(OC(=O)NCC([N:11]1[CH2:16][CH2:15][C:14]([CH2:25][NH2:26])([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=O)(C)(C)C.[NH2:28][C:29]1[C:30]([C:37]([NH:39][C:40](=[NH:43])SC)=[O:38])=[N:31][C:32]([Cl:36])=[C:33]([NH2:35])[N:34]=1>O1CCCC1>[NH2:31][CH2:30][C:37]([N:26]([CH2:25][C:14]1([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)[C:40]([NH:39][C:37]([C:30]1[C:29]([NH2:28])=[N:34][C:33]([NH2:35])=[C:32]([Cl:36])[N:31]=1)=[O:38])=[NH:43])=[O:38]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 130 mg (0.35 mmol) [2-(4-aminomethyl-4-phenethyl-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (A.50) and 80 mg (0.3 mmol) 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea in 5 ml tetrahydrofuran is stirred at 70° C. overnight. Then the reaction mixture is concentrated under reduced pressure and the residue is purified via preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.). Fractions containing the title compound were concentrated under reduced pressure. Then the residue is co-evaporated with methanolic hydrochloric acid in order to remove the protecting group.

Workup

concentrationThen the reaction mixture is concentrated under reduced pressure
customthe residue is purified via preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.)
additionFractions containing the title compound
concentrationwere concentrated under reduced pressure
customto remove the protecting group

Sources & evidence

ORD record: ord-158d70daa4a1467ebb2c791b986bc622
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759349B2

Reaction notes

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