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

HRID 2415624노트

반응식

HRID 2415624 반응식
[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]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2회HCID 757711-Hydroxybenzotriazole2회HCID 27733393-Bromo-5-fluorobenzoic acid2회HCID 178477879HCID 178477879, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5943b607e0cc4c4e93bc005d7173c960
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06818772B2

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