Methanol → 2-[2-(4-Bromo-phenoxy)-acetylamino]-isonicotinamide

HRID 1945457

反応式

HRID 1945457 の反応式
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[C:4](Cl)[CH:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][N:23]=1)[C:18]([NH2:20])=[O:19].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CO>CN(C1C=CN=CC=1)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][N:23]=2)[C:18]([NH2:20])=[O:19])=[O:10])=[CH:11][CH:12]=1

参加物

7

反応物 4

HCID 887MethanolHCID 3516532-AminoisonicotinamideHCID 6931572-(4-Bromo-2-chlorophenoxy)acetic acidHCID 2724699PyBOP

生成物 1

HCID 580013402-[2-(4-Bromo-phenoxy)-acetylamino]-isonicotinamide収率 58.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To solution of (4-bromo-2-chloro-phenoxy)-acetic acid (100 mg, 0.37 mmol), 2-amino isonicotinamide (77.89 mg, 0.56 mmol) and DMAP (92.58 mg, 0.75 mmol) in DMF 5 ml was added PyBOP (394.3 mg, 0.75 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtoAC:Hexane:MeOH=3:6:1˜2:4:1) to afford 2-[2-(4-bromo-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.076 g, 52% yield).

後処理

  1. customReaction mixture
  2. additionwas poured onto ice cold water
  3. customThe organic phase was separated
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by PLC (EtoAC:Hexane:MeOH=3:6:1˜2:4:1)

出典と根拠

ORDレコード
ord-e421505c5c9042058fd3342e659c3a8c
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

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