1,2-Dichloroethane → HCID 71543409, compound

HRID 1749374Notes

Reaction equation

HRID 1749374 reaction equation
[N:1]1[N:2]([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[N:3]=[CH:4][CH:5]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl.Cl.[CH3:30][C@H:31]1[NH:36][CH2:35][C@H:34]([O:37][C:38]2[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[CH:40][N:39]=2)[CH2:33][CH2:32]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:30][C@H:31]1[N:36]([C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:2]2[N:1]=[CH:5][CH:4]=[N:3]2)=[O:10])[CH2:35][C@H:34]([O:37][C:38]2[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[CH:40][N:39]=2)[CH2:33][CH2:32]1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acidHCID 86681868HCID 86681868, compound

Product 1

HCID 71543409HCID 71543409, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(2H-1,2,3-triazol-2-yl)benzoic acid (2.46 g, 13.0 mmol) (prepared as described in WO2008/147518, WO2009/143033 and WO2010/048012), 1-hydroxy-7-azabenzotriazole (1.77 g, 13.0 mmol), and EDC (2.95 g, 15.4 mmol) in DMF (20 mL) was stirred for 5 min. A solution of 2-{[(3R,6R)-6-methylpiperidin-3-yl]oxy}pyridine-4-carbonitrile hydrochloride (3.0 g, 11.8 mmol) in DMF (20 mL) and Hunig's Base (6.20 ml, 35.5 mmol) was added quickly dropwise via addition funnel. The reaction was stirred at RT overnight, then diluted with saturated, aqueous NaHCO3 and water and extracted with EtOAc. The organics were washed with brine, dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography (0-75% ethyl acetate in hexanes), providing the titled compound as a white foam. HRMS m/z (M+H) 389.1714 found, 389.1721 required.

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel gradient chromatography (0-75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c6f7316b6696495994fd437d5950f7bd
Source dataset
uspto-grants-2015_10
Patent number
US09156819B2

Reaction notes

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