1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-bromo-N-{4-((7-chloroquinolin-4-yl)amino)cyclohexyl}-5-fluorobenzamide

HRID 2415624ノート

反応式

HRID 2415624 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][CH2:17][C@@H:16]([NH:19]C4C5C(=CC(Cl)=CC=5)N=CC=4)[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([F:41])[CH:40]=1)[C:35]([OH:37])=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>ClCCl>[Br:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([F:41])[CH:40]=1)[C:35]([NH:19][CH:16]1[CH2:15][CH2:14][CH:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)[CH2:18][CH2:17]1)=[O:37]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2 回HCID 757711-Hydroxybenzotriazole2 回HCID 27733393-Bromo-5-fluorobenzoic acid2 回HCID 178477879HCID 178477879、化合物

生成物 1

HCID 100506923-bromo-N-{4-((7-chloroquinolin-4-yl)amino)cyclohexyl}-5-fluorobenzamide収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 23A cis-N,N′-bis(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine (500 mg, 3.6 mmol), 3-bromo-5-fluorobenzoic acid (600 mg, 5.4 mmol), 1-hydroxybenzotriazole (245 mg, 3.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide(348 mg, 3.6 mmol) in 30 mL dichloromethane was stirred for 3 hours. The reaction was incomplete. 3-bromo-5-fluorobenzoic acid (160 mg, 0.9 mmol), 1-hydroxybenzotriazole (61 mg, 0.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (87 mg, 0.9 mmol) was added and the solution was allowed to stir overnight. The solution was then washed with 1N NaOH, dried (Na2SO4), and concentrated. The residue was purified by flash chromatography (10% methanol in dichloromethane) to provide 700 mg of pure compound, an 81% yield. MS (ESI(+)Q1MS m/z 477 (M+2 H)+; 1H NMR (300 MHz, MeOH) δ ppm 8.36-8.42 (m, 3 H), 7.95 (t, 1 H), 7.69-7.79 (m, 3 H), 7.45 (dd, 1 H), 6.83 (d, 1 H), 6.54 (d, 1 H), 3.95 (m, 1 H), 3.68 (m, 1 H), 1.66-1.98 (m, 8 H).

後処理

  1. stirringto stir overnight
  2. washThe solution was then washed with 1N NaOH
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-5943b607e0cc4c4e93bc005d7173c960
出典データセット
uspto-grants-2004_11
特許番号
US06818772B2

反応ノート

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