Dichloromethane → HCID 67135934, compound

HRID 1631027Notes

Reaction equation

HRID 1631027 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]4[CH3:26])=[C:16]([C:27]([F:30])([F:29])[F:28])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[CH:5][N:4]=1.Cl.[C:32]([O:36][C:37](=[O:41])[CH2:38][NH:39][CH3:40])([CH3:35])([CH3:34])[CH3:33].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O1CCOCC1.O>[CH3:40][N:39]([CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]4[CH3:26])=[C:16]([C:27]([F:30])([F:29])[F:28])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[CH:5][N:4]=1)[CH2:38][C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:41]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 67135827HCID 67135827, compound

Product 1

HCID 67135934HCID 67135934, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-(chloromethyl)pyridin-4-yl)-5-(4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazole (0.065 g; 0.15 mmol), sarcosine t-butyl ester hydrochloride (0.031 g; 0.17 mmol) and K2CO3 (0.046 g; 0.34 mmol) in dioxan (2 mL) was heated at 70° C. for 96 hours. DCM and water were added to the reaction mixture. The mixture was poured through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with DCM/MeOH (100% DCM to 10% MeOH/DCM) to afford the title product. 1H NMR (CDCl3, 400 MHz) δ 8.75 (1H, dd, J=5.1, 0.9 Hz), 8.51 (1 H, d, J=2.1 Hz), 8.34 (1 H, dd, J=8.4, 2.1 Hz), 8.21 (1 H, s), 7.91 (1 H, dd, J=5.1, 1.7 Hz), 7.55 (1 H, d, J=8.4 Hz), 3.98 (2 H, s), 3.34 (2 H, s), 3.12-3.01 (2 H, m), 2.59 (1 H, td, J=11.0, 3.0 Hz), 2.48 (3 H, s), 1.87-1.40 (6 H, m), 1.51 (9 H, s), 0.86 (3 H, d, J=6.2 Hz).

Workup

  1. additionThe mixture was 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 DCM/MeOH (100% DCM to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-8682eb4d48704e349c6932d2b6ccb943
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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