Acrylonitrile → HCID 178432025, compound

HRID 1257676Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(4-methyl-piperidin-4-yl)-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene (75.0 mg, 0.29 mmol) and acrylonitrile (95.5 μL, 1.45 mmol) in ethanol was stirred at 80° C. for 5 hours. The solvent was evaporated under vacuum and the residue purified by column chromatography on silica gel (gradient: 0 to 4.5% [2M NH3 in methanol] in DCM) to afford 64.0 mg (71%) of 3-[4-methyl-4-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-piperidin-1-yl]-propionitrile. LCMS (Method A, ESI): RT=1.91 min, m+H=310.3; 1H NMR (400 MHz, DMSO) δ: 12.41 (s, 1H), 9.04 (s, 1H), 7.59 (t, 1H), 7.08 (m, 1H), 2.85 (m, 2H), 2.66 (m, 4H), 2.58 (m, 2H), 2.49 (m, 2H), 2.11 (m, 2H), 1.85 (s, 3H).

Workup

customThe solvent was evaporated under vacuum
customthe residue purified by column chromatography on silica gel (gradient: 0 to 4.5% [2M NH3 in methanol] in DCM)

Sources & evidence

ORD record: ord-75e10a0455564a498703367af8255923
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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