Butyronitrile → HCID 20583359, compound

HRID 411296Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]([CH2:17][C:18]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:16])[N:7]=[C:6]2[NH2:30].[C:31](#[N:35])[CH2:32][CH2:33][CH3:34]>Cl[Cu].C(O)C>[NH:35]=[C:31]([N:21]1[CH2:20][CH2:19][C:18]([CH2:17][N:15]([CH3:16])[C:8]2[N:7]=[C:6]([NH2:30])[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22]1)[CH2:32][CH2:33][CH3:34]

Participants

Conditions

Temperature: 90 °C

Procedure

To 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (129.8 mg) was added CuCl (31.8 mg), butyronitrile (84 μl), and ethanol (1.0 ml). The reaction mixture was heated in a 90° C. block for one day. Additional CuCl (31.8 mg) and butyronitrile (84 μl) were added and the reaction heated for an additional day. This was chromatographed on silica gel to provide N2-[1-(1-imino-butyl)-4-phenyl-piperidin-4-ylmethyl]-6,7-dimethoxy-N2-methyl-quinazoline-2,4-diamine 17 as indicated by 1HNMR and MS: 477 ([M+H]+). This material was further purified by preparative HPLC to afford the corresponding trifluoroacetic acid salt.

Workup

temperaturethe reaction heated for an additional day
customThis was chromatographed on silica gel

Sources & evidence

ORD record: ord-4b9b4ca2e6fc42a28021f0e1ec0b3d3d
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559153B2

Reaction notes

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