Triethylamine → (S)-tert-butyl (1-(5-bromo-2-(1H-1,2,4-triazol-1-yl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170356Notes

Reaction equation

[Br:1][C:2]1[C:3]([C@@H:12]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[NH:30]1[CH:34]=[N:33][CH:32]=[N:31]1.C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[C:3]([C@@H:12]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[N:4][C:5]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave tube were charged with compound 23B (100 mg, 0.2 mmol), 1H-1,2,4-triazole (42 mg, 0.6 mmol), triethylamine (84 μL, 0.6 mmol) and DMF (0.6 mL, The mixture was heated up to 120° C. for 15 min in a Microwave Synthesizer. After cooled down, it was partitioned between ethyl acetate and 5% of LiCl aqueous solution. The organic layer was separated and concentrated. The residue was purified on silica gel chromatography eluting with ethyl acetate and hexanes to afford the title compound. MS (m/z) 481.21 [M+H]+.

Workup

temperatureAfter cooled down
customit was partitioned between ethyl acetate and 5% of LiCl aqueous solution
customThe organic layer was separated
concentrationconcentrated
customThe residue was purified on silica gel chromatography
washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record: ord-ec00d70c8fe542ddbb353012489ffe9b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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