Triethylamine → 3,3-Dimethyl-4-({1-[3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)morpholine

HRID 517765Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole (80 mg, 0.305 mmol, commercially available from Otava, Kiev, Ukraine) in acetonitrile (2 mL) was added 3,3-dimethylmorpholine (46.2 mg, 0.305 mmol, commercially available, for example from Otava, Kiev, Ukraine or Tyger Scientific, Ewing, USA) and triethylamine (0.127 mL, 0.914 mmol). The reaction mixture was then heated to 120° C. for 50 min in a microwave reactor. The reaction mixture was concentrated in vacuo and the crude product was purified by MDAP. The relevant fractions were combined and concentrated in vacuo. The product was dissolved in DCM and 1N HCl in ether (110 uL) was added. The mixture was concentrated in vacuo, triturated with ether, then dried in vacuo to yield the title compound (white crystals, 40 mg).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe crude product was purified by MDAP
concentrationconcentrated in vacuo
dissolutionThe product was dissolved in DCM
addition1N HCl in ether (110 uL) was added
concentrationThe mixture was concentrated in vacuo
customtriturated with ether
customdried in vacuo

Sources & evidence

ORD record: ord-b149956c8e5248e0a5d0c0328eed6232
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115132B2

Reaction notes

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