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

HRID 1945459

반응식

HRID 1945459 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 580013282-(2-p-Tolyloxy-acetylamino)-isonicotinamide수율 66.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dbe575c5a0e64973b1006d20f25ef636
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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