Hydrochloric Acid → HCID 25256651, compound

HRID 219938Notes

Reaction equation

HRID 219938 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.[CH:39]1([CH2:42]O)[CH2:41][CH2:40]1>>[CH:39]1([CH2:42][O:31][CH2:30][C:19]2[CH:18]=[C:17]([C:15]3[O:14][N:13]=[C:12]([C:10]4[CH:9]=[CH:8][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:11]=4)[N:16]=3)[CH:22]=[CH:21][C:20]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:41][CH2:40]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 75644CyclopropanemethanolHCID 86645656HCID 86645656, compound

Product 1

HCID 25256651HCID 25256651, compound

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 cyclopropylmethanol (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) 13.63 (br s, 1H), 8.35 (d, J=1.5 Hz, 1H), 8.18 (dd, J=7.8, 1.9 Hz, 1H), 8.13-8.08 (m, 1H), 8.04 (dd, J=8.0, 1.4 Hz, 1H), 7.96 (dd, J=11.1, 1.2 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 7.36-7.26 (m, 3H), 7.15 (d, J=7.2 Hz, 1H), 4.30-4.20 (m, 2H), 3.20-3.17 (m, 2H), 2.04 (s, 3H), 1-0.91 (m, 1H), 0.46-40 (m, 2H), 0.14-0.09 (m, 2H). LC/MS (Method B): 457.3 (M−H)−, 459.2 (M+H)+. HPLC (Method A) Rt 5.67 min (Purity: 98.5%).

Workup

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

Sources & evidence

ORD record
ord-e74204b999e84aeca12eb34110422f2b
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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