Acrylonitrile → HCID 59190824, compound

HRID 418338Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:28])[NH:17][C:18]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][NH:24][CH2:25]3)=[CH:20][CH:19]=2)[CH:11]=1)=[O:7].[C:34](#[N:37])[CH:35]=[CH2:36]>C1(C)C=CC=CC=1>[C:34]([CH2:35][CH2:36][N:24]1[CH2:23][CH2:22][C:21]2[C:26](=[CH:27][C:18]([NH:17][C:16]([C:12]3[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=3)[CH2:9][NH:8][C:6](=[O:7])[C:5]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:28])=[CH:19][CH:20]=2)[CH2:25]1)#[N:37]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolved 3,4-dimethoxy-N-[3-(1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide (50.0 mg, 0.12 mmol) in 3 mL of toluene and added acrylonitrile (0.04 mL, 0.600 mmol). The mixture was heated at 80° C. for 2 h. LC-MS indicated the desired material. Concentrated to dryness and applied to a SiO2 prep plate. Eluted with (5% MeOH/1% NH3/CH2Cl2) to give 40.8 mg of N-{3-[2-(2-Cyano-ethyl)-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl]-benzyl}-3,4-dimethoxy-benzamide. MS, electrospray 499.5 (M+H).

Workup

concentrationConcentrated to dryness
washEluted with (5% MeOH/1% NH3/CH2Cl2)

Sources & evidence

ORD record: ord-1be0cac1175b4f26877d9e9669f65f35
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093266B2

Reaction notes

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