Dichloromethane → HCID 46908239, compound

HRID 1631031Notes

Reaction equation

HRID 1631031 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]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])=[C:16]([CH2:27][O:28][CH3:29])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[CH:5][N:4]=1.Cl.C([O:35][C:36](=[O:40])[CH2:37][NH:38][CH3:39])(C)(C)C.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O1CCOCC1.O>[CH3:29][O:28][CH2:27][C:16]1[CH:15]=[C:14]([C:12]2[O:11][N:10]=[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][N:38]([CH3:39])[CH2:37][C:36]([OH:40])=[O:35])[CH:8]=3)[N:13]=2)[CH:19]=[CH:18][C:17]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 67135927HCID 67135927, compound

Product 1

HCID 46908239HCID 46908239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-(2-(chloromethyl)pyridin-4-yl)-5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazole (0.097 g; 0.24 mmol), sarcosine t-butyl ester hydrochloride (0.037 g; 0.27 mmol) and K2CO3 (0.043 g; 0.27 mmol) in dioxan (3 mL) was heated at 70° C. for 7 days. DCM and water were added to the reaction mixture. The mixture was poured through a hydrophobic frit. The solvent was evaporated in vacuo. The material was purified by SCX chromatography and the material treated with HCl solution in dioxan (5 M; 3 mL) and the reaction mixture stirred at 70° C. for 18 hours. The solvent was evaporated in vacuo and the residue purified by preparative HPLC, affording the title product as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.78 (1 H, d, J=5.1 Hz), 8.42 (1 H, s), 8.16 (1 H, dd, J=8.2, 2.0 Hz), 8.08 (1 H, s), 8.04 (1 H, dd, J=5.2, 1.5 Hz), 7.38-7.21 (4 H, m), 7.12 (1 H, d, J=7.4 Hz), 5.39 (1 H, br s), 4.23 (2 H, dd, J=17.0, 12.7 Hz), 4.17 (2 H, s), 3.54 (2 H, s), 3.34 (3 H, s), 2.66 (3 H, s), 2.08 (3 H, s). LC/MS: 388 (M+H)+. HPLC (Method B) Rt 2.97 min (Purity: 99.2

Workup

  1. additionThe mixture was poured through a hydrophobic frit
  2. customThe solvent was evaporated in vacuo
  3. customThe material was purified by SCX chromatography
  4. additionthe material treated with HCl solution in dioxan (5 M; 3 mL)
  5. customThe solvent was evaporated in vacuo
  6. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-ed72b659151547629509fd277e24ac5e
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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