Triethylamine → HCID 178521836、化合物

HRID 1666342

反応式

HRID 1666342 の反応式
[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

参加物

6

反応物 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

生成物 1

HCID 178521836HCID 178521836、化合物収率 47%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fc2dcedb90a34263b2c1a31e5f7d4a3b
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

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