Hydrochloric Acid → HCID 59495710, compound

HRID 219937Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

Methyl 2-fluoro-4-[5-(2′-methyl-2-{[(methylsulfonyl)oxy]methyl}biphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzoate, prepared as in example 58, step 1, (75 mg; 0.15 mmol) was dissolved in 2-methyl-1-propanol (5 mL). The solution was then heated in the microwave at 130° C. for 10 min. Sodium hydroxide (151.05 μL; 5 M; 0.76 mmol) was added and the mixture was heated at 60° C. for 10 min in the microwave. Hydrogen chloride (151.05 μL; 5 M; 0.76 mmol) was added and the mixture was evaporated to dryness. The crude was purified with MD Autoprep, to afford the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 13.63 (br s, 1H), 8.34 (d, J=1.5 Hz, 1H), 8.18 (dd, J=8.0, 1.8 Hz, 1H), 8.13-8.08 (m, 1H), 8.03 (dd, J=8.1, 1.4 Hz, 1H), 7.95 (dd, J=11.0, 1.2 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 7.36-7.25 (m, 3H), 7.15 (d, J=7.0 Hz, 1H), 4.23 (s, 2H), 3.10 (d, J=6.4 Hz, 2H), 2.04 (s, 3H), 1.77 (sept, J=6.6 Hz, 1H), 0.84 (d, J=6.6 Hz, 6H). LC/MS (Method B): 459.4 (M−H)−, 461.3 (M+H)+. HPLC (Method A) Rt 6.04 min (Purity: 99.3%).

Workup

temperaturethe mixture was heated at 60° C. for 10 min in the microwave
customthe mixture was evaporated to dryness
customThe crude was purified with MD Autoprep

Sources & evidence

ORD record: ord-368550ce76db4f189a61e418fb42b465
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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