Triethylamine → 2-(4-tert-Butylphenyl)-N-((3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)acetamide

HRID 877379

反応式

HRID 877379 の反応式
[Cl-].[F:2][C:3]1[CH:4]=[C:5]([CH:10]([C:12]2[N:13]=[N:14][N:15]([CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:16]=2)[NH3+:11])[CH:6]=[CH:7][C:8]=1[F:9].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33](O)=[O:34])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>O.C(Cl)Cl>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:11][CH:10]([C:5]2[CH:6]=[CH:7][C:8]([F:9])=[C:3]([F:2])[CH:4]=2)[C:12]2[N:13]=[N:14][N:15]([CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:16]=2)=[O:34])=[CH:30][CH:31]=1)([CH3:25])([CH3:23])[CH3:24]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86668966(3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methanaminium chloride

生成物 1

HCID 671758872-(4-tert-Butylphenyl)-N-((3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)acetamide収率 75.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a 50 ml round bottom flask equipped with a magnetic-stir bar were added (3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methanaminium chloride (0.500 g, 1.502 mmol), 4-tert-butylphenylacetic acid (0.289 mg, 1.502 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.288 g, 1.502 mmol), 1-hydroxy-7-azabenzotriazole (0.204 mg, 1.502 mmol) and triethylamine (0.629 ml, 2.253 mmol) into 10.0 ml of CH2Cl2. The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and the two layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 0.536 g (67%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.347 (m, 2H), 7.190 (m, 3H), 7.040 (m, 2H), 6.970 (m, 2H), 6.223 (d, J=7.60 Hz, 1H), 3.852 (ABq, J=15.29 Hz, 2H), 3.580 (s, 2H), 1.305 (s, 9H), 0.125 (s, 9H). ES-MS [M+1]+: 471.2.

後処理

  1. customTo a 50 ml round bottom flask equipped with a magnetic-stir bar
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuum
  8. customPurification
  9. additionby preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

出典と根拠

ORDレコード
ord-e151b7be13bc499a9a05c452b1f40df8
出典データセット
uspto-grants-2015_03
特許番号
US08987310B2

関連ノート

読み込み中…