Triethylamine → HCID 86691902, compound

HRID 517789Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

4-[5-(Chloromethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (Intermediate 24, 86 mg, 0.3 mmol) and 3,5-dimethyl-1-(methylsulfonyl)piperazine (Intermediate 36, 78 mg, 0.41 mmol) were weighed into a vial and suspended in acetonitrile (1.2 mL). Triethylamine (84 μL, 0.60 mmol) was added, and the mixture was heated at 140° C. in a microwave with stirring for 3 h. The reaction mixture was applied to a 10 g SCX cartridge, pre-washed with MeOH (50 mL). This was eluted with MeOH (100 mL) and 10% aq NH3 in MeOH (100 mL). The basic fractions were concentrated to give an off-white solid (137 mg). This was purified by MDAP to give the title compound as a colourless solid (38 mg), confirmed by NMR to be the pure cis-isomer.

Workup

washpre-washed with MeOH (50 mL)
washThis was eluted with MeOH (100 mL) and 10% aq NH3 in MeOH (100 mL)
concentrationThe basic fractions were concentrated

Sources & evidence

ORD record: ord-820200f9601d422da9aff25fc812bdfd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115132B2

Reaction notes

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