1,2-Dichloroethane → N-[2-(Methyloxy)-3-pyridinyl]-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

HRID 1623794Notes

Reaction equation

HRID 1623794 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:38][O:39][C:40]1[C:45]([NH2:46])=[CH:44][CH:43]=[CH:42][N:41]=1>CN(C)C=O.O.CC#N>[CH3:38][O:39][C:40]1[C:45]([NH:46][C:11](=[O:13])[C:10]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:9]=2[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:44][CH:43]=[CH:42][N:41]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27374883-Amino-2-methoxypyridineHCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

Product 1

HCID 69936233N-[2-(Methyloxy)-3-pyridinyl]-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 110 mg, 0.33 mmol), EDC (126 mg, 0.66 mmol) and HOBT (101 mg, 0.66 mmol) in dimethylformamide (2 ml) was stirred in air at room temperature for 1 h. 2-Methoxy-pyridin-3-amine (40.8 mg, 0.33 mmol) was then added in one charge. The reaction mixture was stirred at 25° C. overnight. The reaction mixture was diluted with water (25 ml) and then extracted with ethyl acetate (60 ml×3). The organic phases were combined, washed by brine (50 ml×3), dried over anhydrous MgSO4, and concentrated. The residue was purified by Prep-HPLC (instrument: Gilson GX-281, Column: Shimadzu 15 μm, 250*20 mm*2, Mobile Phase: A=10 mmol NH4HCO3/water B=CH3CN, Flow rate: 30.0 ml/L method: B=80%-90%, 0.0-7.2 min; B=90%-95%, 7.2-7.5 min; B=95%-95%, 7.5 min-11.5 min, the RT=11.0 min) to yield the title compound as a pink solid. 92 mg.

Workup

  1. additioncharge
  2. extractionextracted with ethyl acetate (60 ml×3)
  3. washwashed by brine (50 ml×3)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by Prep-HPLC (instrument
  7. customB=80%-90%, 0.0-7.2 min
  8. customB=90%-95%, 7.2-7.5 min

Sources & evidence

ORD record
ord-98f8d363bebb4020b8cab69796c32983
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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