1,2-Diaminocyclohexane, trans- → N-[4-amino-3-(4-amino-3-methoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-pyrrolidin-1-ylacetamide triacetate salt

HRID 1270960Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:18])=[N:14][CH:15]=[C:16](I)[C:11]=3[S:10][CH:9]=2)=[CH:4][C:3]=1[O:19][CH3:20].[N:21]1([CH2:26][C:27]([NH2:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]1.P([O-])([O-])([O-])=[O:31].[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.O1CCOCC1>[C:3]([OH:19])(=[O:28])[CH3:4].[C:27]([OH:28])(=[O:31])[CH3:26].[C:3]([OH:19])(=[O:28])[CH3:4].[NH2:18][C:13]1[C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:19][CH3:20])[CH:4]=3)=[CH:9][S:10][C:11]=2[C:16]([NH:29][C:27](=[O:28])[CH2:26][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][N:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A schlenck tube was charged with 3-(4-amino-3-methoxyphenyl)-7-iodothieno[3,2-c]pyridin-4-amine (199 mg,0.5 mmol), 2-pyrrolidin-1-ylacetamide (0.6 mmol), copper(I) iodide (4.8 mg, 0.025 mmol), potassium phosphate (225 mg, 1.06 mmol). Evacuated under vacuum and back filled with nitrogen. trans-Cyclohexane-1,2-diamine (6.5 uL, 0.05 mmol) and dioxane (1 mL) was added. The reaction tube was sealed and heated at about 110° C. overnight. The solvent was removed and the crude product was purified by reverse phase preparative HPLC to give the title compound as the tri-acetate salt. LCMS (Conditions a): MH+=398.2, Rt=1.55 min. (154 mg, 45%)

Workup

customEvacuated under vacuum
additionback filled with nitrogen
customThe reaction tube was sealed
customThe solvent was removed
customthe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-f9eca53e2c614716881b46cc2a7edbe0
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202363B2

Reaction notes

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