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

HRID 1945459

反応式

HRID 1945459 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 580013282-(2-p-Tolyloxy-acetylamino)-isonicotinamide収率 66.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dbe575c5a0e64973b1006d20f25ef636
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

関連ノート

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