Water → HCID 67135927, compound

HRID 1631030Notes

Reaction equation

HRID 1631030 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([CH2:21]O)[CH:16]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C.CS([Cl:43])(=O)=O.O>C(Cl)Cl>[Cl:43][CH2:21][C:17]1[CH:16]=[C:15]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:14][N:13]=2)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67136005HCID 67136005, compound

Product 1

HCID 67135927HCID 67135927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol (0.282 g; 0.73 mmol) and DIEA (0.25 mL; 1.46 mmol) in DCM (6 mL) was added methanesulfonyl chloride (0.062 mL; 0.80 mmol). The mixture was stirred at ambient temperature for 1 hour and water added. The mixture was passed through a hydrophobic frit and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.78 (1 H, d, J=5.1 Hz), 8.44 (1 H, d, J=1.8 Hz), 8.26 (1 H, s), 8.18 (1 H, dd, J=7.9, 1.9 Hz), 8.02 (1 H, dd, J=5.1, 1.5 Hz), 7.37-7.22 (4 H, m), 7.13 (1 H, d, J=7.5 Hz), 4.79 (2 H, s), 4.28-4.18 (2 H, m), 3.34 (3 H, s), 2.08 (3 H, s).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was purified by flash chromatography on silica
  3. washeluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc)

Sources & evidence

ORD record
ord-6523a567fd894669aec417f1b2435299
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

Loading…