Triethylamine → N-(3-(4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)acrylamide

HRID 1522092ノート

反応式

HRID 1522092 の反応式
[O:1]([C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=2)[NH2:22])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:38])[CH:36]=[CH2:37]>CN1CCCC1=O.ClCCl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[C:21]([NH:22][C:35](=[O:38])[CH:36]=[CH2:37])[CH:23]=[CH:24][CH:25]=2)=[CH:26][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 714740103-(4-(4-Phenoxyphenoxy)pyridin-3-yl)aniline

生成物 1

HCID 86721736N-(3-(4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)acrylamide収率 36.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

Into a 20 mL vial was placed 3-(4-(4-phenoxyphenoxy)pyridin-3-yl)aniline (30.00 mg, 0.08 mmol), N,N-diethylethanamine (0.02 mL, 0.17 mmol) suspended in 1-methylpyrrolidin-2-one (0.35 mL) and dichloromethane (2.00 mL). The resulting mixture was cooled to 0° C. Added acryloyl chloride (0.02 mL, 0.25 mmol). The ice bath was left to melt and the reaction mixture was stirred at rt overnight. The reaction mixture was purified using Biotage column chromatography eluting 0-40% MeOH in EtOAc. Fractions containing the desired product were combined and concentrated. Purified using prep-HPLC eluting 25-55% CH3CN in 0.1% TFA in H2O. Fractions containing the desired product were combined and lyophilized overnight to afford N-(3-(4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)acrylamide as a white solid (12.00 mg, 35% yield). HPLC purity: 100%, RT=4.235 min. MS: m/z=409 [M+H]+, RT=3.38 min. 1H-NMR (DMSO-d6) δ 10.23 (s, 1H), 8.52 (s, 1H), 8.43 (d, 1H), 7.95 (s, 1H), 7.71 (d, 1H), 7.44-7.33 (m, 4H), 7.19 (d, 2H), 7.13 (t, 1H), 7.09 (d, 2H), 7.02 (d, 2H), 6.80 (d, 1H), 6.45 (dd, 1H), 6.26 (d, 1H), 5.75 (d, 1H).

後処理

  1. customThe reaction mixture was purified
  2. washeluting 0-40% MeOH in EtOAc
  3. additionFractions containing the desired product
  4. concentrationconcentrated
  5. customPurified
  6. washusing prep-HPLC eluting 25-55% CH3CN in 0.1% TFA in H2O
  7. additionFractions containing the desired product
  8. waitlyophilized overnight

出典と根拠

ORDレコード
ord-255757d2718e4781b3ba2f4fe2a23884
出典データセット
uspto-grants-2015_07
特許番号
US09073947B2

反応ノート

読み込み中…