Triethylamine → HCID 178521836, 화합물

HRID 1666342

반응식

HRID 1666342 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11](=[O:19])OC3C=CC=CC=3)=[CH:9][C:4]=2[N:3]=[N:2]1.Cl.[NH:21]1[CH2:26][CH2:25][C:24](=[CH:27][C:28]2[CH:29]=[C:30]([CH:42]=[CH:43][CH:44]=2)[O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][N:33]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C.CCOC(C)=O>CS(C)=O>[NH:3]1[C:4]2[CH:9]=[C:8]([NH:10][C:11]([N:21]3[CH2:26][CH2:25][C:24](=[CH:27][C:28]4[CH:44]=[CH:43][CH:42]=[C:30]([O:31][C:32]5[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][N:33]=5)[CH:29]=4)[CH2:23][CH2:22]3)=[O:19])[CH:7]=[CH:6][C:5]=2[N:1]=[N:2]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochlorideHCID 178521835Phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamate

생성물 1

HCID 178521836HCID 178521836, 화합물수율 47%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

To a solution of phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamate (0.15 g, 0.62 mmol, from Step 1) in DMSO (5 mL) was added 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.23 g, 0.62 mmol) (from Example 1, Step 5), followed by triethylamine (0.16 mL, 1.2 mmol). The reaction was stirred at 60° C. overnight. The reaction was cooled down and EtOAc (30 mL) was added. The organic layer was washed with water, saturated NH4Cl, and brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by column chromatography (0-5% MeOH/CH2Cl2) gave the desired compound as a foam (144 mg). MS (M+1): 495.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76-8.80 (m, 1H) 8.54-8.56 (m, 1H) 8.20 (dd, 1H) 8.01-8.04 (m, 1H) 7.76-7.82 (m, 1H) 7.37-7.42 (m, 2H) 7.21 (d, 1H) 7.13 (d, 1H) 7.02-7.05 (m, 2H) 6.37-6.40 (m, 1H) 3.56 (t, 2H) 3.48 (t, 2H) 3.28-3.30 (m, 1H) 2.50-2.51 (m, 1H) 2.33-2.38 (m, 2H).

후처리

  1. temperatureThe reaction was cooled down
  2. washThe organic layer was washed with water, saturated NH4Cl, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (0-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-fc2dcedb90a34263b2c1a31e5f7d4a3b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

연결된 노트

불러오는 중…