6-(Trifluoromethyl)pyridine-3-carboxaldehyde → 2-Cyclopentyl-N-{2,6-dimethyl-4-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-phenyl}-acetamide

HRID 1820154노트

반응식

HRID 1820154 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:17])[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:4]([CH3:18])[CH:3]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[N:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1>C(#N)C>[CH:12]1([CH2:11][C:10]([NH:9][C:5]2[C:4]([CH3:18])=[CH:3][C:2]([NH:1][CH2:27][C:24]3[CH:25]=[N:26][C:21]([C:20]([F:30])([F:19])[F:29])=[CH:22][CH:23]=3)=[CH:7][C:6]=2[CH3:8])=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

4

반응물 2

HCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 68707920N-(4-Amino-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

생성물 1

HCID 115965852-Cyclopentyl-N-{2,6-dimethyl-4-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-phenyl}-acetamide수율 92.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
150 °C

실험 절차

N-(4-Amino-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (204 mg) and 6-trifluoromethyl-pyridine-3-carbaldehyde (163 mg) were dissolved in acetonitrile (3 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo, redissolved in methanol (5 mL) followed by addition of acetic acid (0.5 mL) and sodium cyanoborohydride (244 mg) and stirred at 25° C. for 16 hours. Aqueous sodium carbonate (10%, 25 mL) was added, and the product was collected by filtration to furnish 0.311 g (92% yield) of the title compound as a white solid. LC-MS (m/z) 406 (MH+); tR=2.90, (UV, ELSD) 98%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.20 (m, 2H), 1.51 (m, 2H), 1.60 (m, 2H), 1.75 (m, 2H), 1.97 (s, 6H), 2.22 (m, 3H), 4.39 (d, 2H), 6.20 (t, 1H), 6.28 (s, 2H), 7.85 (d, 1H), 7.99 (d, 1H), 8.75 (s, 1H), 8.77 (s, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in methanol (5 mL)
  3. additionfollowed by addition of acetic acid (0.5 mL) and sodium cyanoborohydride (244 mg)
  4. additionAqueous sodium carbonate (10%, 25 mL) was added
  5. filtrationthe product was collected by filtration

출처 및 근거

ORD 기록
ord-9159aa530fa14b4e88771ab3f96a8528
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601870B2

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