Acetonitrile → HCID 86729369, compound

HRID 521207Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][NH:8][C:9]=1[NH2:10])=[O:4].[C:11]([CH:13]=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)#[N:12].C(#N)C.C[O-].[Na+]>O.CN(C=O)C>[NH2:10][C:9]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][N:7]([C:14]2([CH2:13][C:11]#[N:12])[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:18][CH2:19]2)[N:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a flask containing 5-amino-1H-pyrazole-4-carboxylic acid methyl ester (2.0 g, 14 mmol) was added tert-butyl 4-(cyanomethylidene)piperidine-1-carboxylate (6.3 g, 28 mmol), acetonitrile (57 mL), and DMF (25 mL), followed by the addition of catalytic NaOMe (0.10 g, 2.1 mmol). The mixture was heated to 70° C. and allowed to stir for 18 hours. The mixture was then allowed to cool to ambient temperature, diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-10% MeOH/DCM) to afford the title compound. LRMS (ESI) calc'd for C17H26N5O4 [M+H]+: 364. Found: 364.

Workup

temperatureto cool to ambient temperature
extractionextracted with EtOAc (2×)
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by MPLC on silica gel (
washa gradient elution of 0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-e63c8ee6b0aa4a948ac9bb77ebe19799
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328099B2

Reaction notes

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