Water → Methyl 3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate

HRID 337057Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH:18][C:19]2[C:20](=[O:37])[N:21]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=3[CH3:36])[C:29]([O:31][CH3:32])=[O:30])[CH:22]=[C:23](Br)[N:24]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1.C([O-])=O.[NH4+].ClCCl.O>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH:18][C:19]2[C:20](=[O:37])[N:21]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=3[CH3:36])[C:29]([O:31][CH3:32])=[O:30])[CH:22]=[CH:23][N:24]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 75 °C

Procedure

To Methyl 3-(3-(1-(2-(benzyloxy)phenyl)cyclopropylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate (Example 167b, 543 mg) in ethanol (15 mL) was added ammonium formate (855 mg) and 10% Pd/C (103 mg) and the reaction was heated at 75° C. for 1 h. The mixture was filtered through celite and the solids washed with ethanol. The filtrate was collected and the volatiles removed in vacuo to give a pale yellow solid. Dichloromethane and water were added and the organic layer separated. The aqueous layer was further extracted with dichloromethane and ethyl acetate. The combined organic extracts were dried (Na2SO4) and the solvent removed in vacuo to give the subtitle product an off white foam (331 mg).

Workup

filtrationThe mixture was filtered through celite
washthe solids washed with ethanol
customThe filtrate was collected
customthe volatiles removed in vacuo
customto give a pale yellow solid
customthe organic layer separated
extractionThe aqueous layer was further extracted with dichloromethane and ethyl acetate
dry with materialThe combined organic extracts were dried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-94e6ecb8e5b44fddb885fc5f3d225eab
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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