2-(4-Tert-butylphenoxy)acetic acid → 2-[2-(4-Tert-butyl-phenoxy)-acetylamino]-isonicotinamide

HRID 1945458

Reaction equation

HRID 1945458 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][N:25]=1)[C:20]([NH2:22])=[O:21].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:16][C:17]2[CH:18]=[C:19]([CH:23]=[CH:24][N:25]=2)[C:20]([NH2:22])=[O:21])=[O:13])=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 81531DiisopropylethylamineHCID 3516532-AminoisonicotinamideHCID 2724699PyBOP

Product 1

HCID 442186532-[2-(4-Tert-butyl-phenoxy)-acetylamino]-isonicotinamideYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-tert-butylphenoxy acetic acid (60.1 mg, 0.29 mmol), 2-amino isonicotinamide (60.3 mg, 0.44 mmol), DIPEA (0.1 ml, 0.58 mmol) and PyBOP (301.8 mg, 0.58 mmol) in DMF 4.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1) to give 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinamide as a white solid (53.6 mg, 56.5% yield).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-a0d3027d71c24f2ea89ebae75ab096c4
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Linked notes

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