Water → HCID 67135827, compound

HRID 1631026Notes

Reaction equation

HRID 1631026 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH2:25]O)[CH:20]=3)[N:15]=2)=[CH:10][C:9]=1[C:27]([F:30])([F:29])[F:28].CCN(C(C)C)C(C)C.CS([Cl:44])(=O)=O.O>C(Cl)Cl>[Cl:44][CH2:25][C:21]1[CH:20]=[C:19]([C:16]2[N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([N:3]4[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]4[CH3:1])=[C:9]([C:27]([F:30])([F:28])[F:29])[CH:10]=3)[O:18][N:17]=2)[CH:24]=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67135173HCID 67135173, compound

Product 1

HCID 67135827HCID 67135827, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(5-(4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol (0.125 g; 0.30 mmol) and DIEA (0.10 mL; 0.60 mmol) in DCM (2.5 mL) was added methanesulfonyl chloride (0.026 mL; 0.33 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Water was added to the reaction mixture and the mixture poured through a hydrophobic frit. 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 product (0.129 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 8.77 (1 H, dd, J=5.1, 0.9 Hz), 8.51 (1 H, d, J=2.1 Hz), 8.34 (1H, dd, J=8.4, 2.1 Hz), 8.23 (1 H, s), 7.99 (1 H, dd, J=5.1, 1.6 Hz), 7.56 (1 H, d, J=8.4 Hz), 4.78 (2 H, s), 3.12-3.03 (2 H, m), 2.59 (1 H, td, J=11.0, 3.1 Hz), 1.86-1.62 (4 H, m), 1.53-1.38 (2 H, m), 0.86 (3 H, d, J=6.2 Hz).

Workup

  1. additionthe mixture poured through a hydrophobic frit
  2. customThe solvent was evaporated in vacuo
  3. customThe residue was purified by flash chromatography on silica
  4. washeluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc)

Sources & evidence

ORD record
ord-83c7b42e4ee148b2a8a3d2fed55b011b
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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