Dimethylamine → US9115126, Example 35

HRID 517989Notes

Reaction equation

CS(OCCCOC1C=[CH:14][C:13]([C:16]2C=[C:18]([C:26]#[N:27])[C:19]3[N:23]=[N:22][N:21]([CH3:24])[C:20]=3[CH:25]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29])(=O)=O.[CH:32]([N:35]([CH:38](C)C)[CH2:36]C)(C)C.C[NH:42]C.[CH2:44]1[CH2:48][O:47][CH2:46][CH2:45]1>>[CH3:32][N:35]([CH3:38])[CH2:36][CH2:44][CH2:48][O:47][C:46]1[CH:45]=[CH:14][C:13]([C:16]2[N:42]=[C:18]([C:26]#[N:27])[C:19]3[N:23]=[N:22][N:21]([CH3:24])[C:20]=3[CH:25]=2)=[CH:12][C:11]=1[C:28]([F:29])([F:30])[F:31]

Participants

Reactant 4

HCID 674Dimethylamine

HCID 8028Tetrahydrofuran

HCID 81531Diisopropylethylamine

HCID 866733533-(4-(4-cyano-1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

Product 1

HCID 53330392US9115126, Example 35

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(4-(4-cyano-1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-2-(trifluoro-methyl)phenoxy)propyl methanesulfonate (20 mg), diisopropylethylamine (73 μl) and dimethylamine in THF (2M, 1 ml) was heated at 100° C. under microwave conditions for 20 minutes. The mixture was purified by HPLC to give the expected product (6.3 mg).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-f496b8a22efa47968c2c9382b6029aa4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115126B2

Reaction notes

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