Potassium Phosphate, Tribasic → {1-[5-(Cyclopropanecarbonyl-amino)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester

HRID 1040436Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:19]1([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O.[Cu]I>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14]([NH:24][C:22]([CH:19]3[CH2:21][CH2:20]3)=[O:23])=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 0.20 g (0.56 mmol) of [1-(5-iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester, 22 mg (0.12 mmol) of CuI, 0.035 mL (0.22 mmol) of 1,2-trans-di(methylamino)cychlohexane, 0.090 mg (1.1 mmol) of cyclopropanecarboxamide, and 0.24 mg (1.1 mmol) of K3PO4 in 1 mL of 1,4-dioxane was heated under an N2 atmosphere for overnight at 110° C. The mixture was cooled, diluted with 10 mL of EtOAc, and washed with aq. NH4Cl/NH4OH (pH 8), then with aq. NH4Cl. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was triturated with acetonitrile to provide 98 mg (56%) of {1-[5-(cyclopropanecarbonyl-amino)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester as an off-white powder.

Workup

temperatureThe mixture was cooled
washwashed with aq. NH4Cl/NH4OH (pH 8)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was triturated with acetonitrile

Sources & evidence

ORD record: ord-e7546771334f4477b216afcc510f0db2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552205B2

Reaction notes

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