p-Methylphenoxyacetic acid → 2-(2-p-Tolyloxy-acetylamino)-isonicotinamide

HRID 1945459

Reaktionsgleichung

Reaktionsgleichung von HRID 1945459
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([OH:11])=O)=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][N:22]=1)[C:17]([NH2:19])=[O:18].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]1([CH3:12])[CH:2]=[CH:3][C:4]([O:7][CH2:8][C:9]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][N:22]=2)[C:17]([NH2:19])=[O:18])=[O:11])=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 70329p-Methylphenoxyacetic acidHCID 81531DiisopropylethylamineHCID 3516532-AminoisonicotinamideHCID 2724699PyBOP

Produkt 1

HCID 580013282-(2-p-Tolyloxy-acetylamino)-isonicotinamideAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4 p-tolyloxy-acetic acid (60.1 mg, 0.36 mmol), 2-amino-isonicotinamide (74.1 mg, 0.54 mmol), DIPEA (0.12 ml, 0.72 mmol) and PyBOP (374.4 mg, 0.72 mmol) in DMF 5.0 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(CH2Cl2:MeOH=10:1) to give 2-(2-p-tolyloxy-acetylamino)-isonicotinamide as a white solid (68.5 mg, 66.8% yield).

Aufarbeitung

  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(CH2Cl2:MeOH=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-dbe575c5a0e64973b1006d20f25ef636
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394799B2

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