Water → HCID 86645656, compound

HRID 219936Notes

Reaction equation

HRID 219936 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][OH:31])[CH:18]=3)[O:14][N:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O>C(Cl)Cl>[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:42]([CH3:41])(=[O:44])=[O:43])[CH:18]=3)[O:14][N:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67529101HCID 67529101, compound

Product 1

HCID 86645656HCID 86645656, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., into a solution of methyl 2-fluoro-4-{5-[2-(hydroxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate, prepared as in example 58, step 1, (500 mg; 1.19 mmol) in DCM (15 mL) was added DIEA (610 μL; 3.58 mmol) and methanesulfonyl chloride (139 μL; 1.79 mmol). The reaction was allowed to warm to RT for 2 h30. Water (5 mL) was added and the DCM extract was rapidly washed twice more with water. The organic layer was then dried over magnesium sulfate, filtered and concentrated to afford the title compound as a yellow foam (573 mg; 97%). 1H NMR (DMSO-d6, 300 MHz) δ 8.47 (d, J=1.8 Hz, 1H), 8.30 (dd, J=8.0, 1.8 Hz, 1H), 8.18-8.13 (m, 1H), 8.09 (dd, J=8.1, 1.5 Hz, 1H), 8.02 (dd, J=11.2, 1.4 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.40-7.29 (m, 3H), 7.19 (d, J=7.0 Hz, 1H), 5.11 (d, J=11.4 Hz, 1H), 5.05 (d, J=11.4 Hz, 1H), 3.92 (s, 3H), 3.04 (s, 3H), 2.05 (s, 3H). LC/MS (Method B): 497.3 (M+H)+. HPLC (Method A) Rt 5.52 min (Purity: 96.7%).

Workup

  1. extractionthe DCM extract
  2. washwas rapidly washed twice more with water
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3f503c9b5e0e40f9a1284f95c8ecde59
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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