Diisopropylethylamine → N-[(S)-1-(3-methoxy-phenyl)ethyl]-4-pyridin-4-yl-benzamide

HRID 2094828Notes

Reaction equation

HRID 2094828 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C@@H:24]([NH2:26])[CH3:25])[CH:21]=[CH:22][CH:23]=1.CCN(C(C)C)C(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C@@H:24]([NH:26][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:15][CH:14]=2)[CH3:25])[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 15208114-(Pyridin-4-yl)benzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7020761(S)-1-(3-methoxyphenyl)ethylamine

Product 1

HCID 68516150N-[(S)-1-(3-methoxy-phenyl)ethyl]-4-pyridin-4-yl-benzamideYield 66.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(pyridin-4-yl)benzoic acid (0.970 g, 4.87 mmol), (S)-1-(3-methoxyphenyl)ethanamine (0.884 g, 5.84 mmol), DIEA (1.7 ml, 9.8 mmol), and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.87 g, 5.82 mmol) in DMF (10 ml) was stirred overnight, diluted with EtOAc, washed with 1N NaOH, sat NaHCO3, and brine, dried (Na2SO4), and chromatographed (20-85% EtOAc/dichloromethane) and triturated (Et2O) to give the title compound (1.075 g, 3.23 mmol) as a white solid.

Workup

  1. washwashed with 1N NaOH
  2. dry with materialdried (Na2SO4)
  3. customchromatographed (20-85% EtOAc/dichloromethane)
  4. customtriturated (Et2O)

Sources & evidence

ORD record
ord-7132d38b591a410698eb92fbc9d14694
Source dataset
uspto-grants-2013_05
Patent number
US08445686B2

Reaction notes

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