Hydrochloric Acid → HCID 86601236, 화합물

HRID 349283

반응식

HRID 349283 반응식
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.CON(C)[C:21]([C:23]1[N:24]=[N:25][N:26]([CH2:34][C:35]2[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=2)[C:27]=1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:22].Cl>C1COCC1.CCOCC.CCOC(C)=O>[F:44][C:41]([F:42])([F:43])[C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([C:45]([F:46])([F:48])[F:47])[CH:38]=1)[CH2:34][N:26]1[C:27]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:23]([C:21]([C:14]2[N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[Cl:6])[CH:17]=[CH:16][N:15]=2)=[O:22])[N:24]=[N:25]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1428581-(2-Chlorophenyl)imidazoleHCID 866012371-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid methoxy-methyl-amideHCID 178418339Butyllithium

생성물 1

HCID 86601236HCID 86601236, 화합물

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

Add BuLi (0.80 mL, 1.28 mmol) to a −78° C. solution of 1-(2-chloro-phenyl)-1H-imidazole (200 mg, 1.12 mmol) in THF (3 mL). Stir at −78° C. for 20 min., then add a solution of 1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid methoxy-methyl-amide (261 mg, 0.57 mmol) in THF (2 mL) via cannula. Stir the resulting solution at −78° C. for 10 min., then allow to warm to RT and stir for 2 h. Add 1N HCl (1.3 mL) and stir for 30 min. Dilute reaction with EtOAc (50 mL) and wash with water (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). Dry, filter and concentrate the organic solution and purify the crude material by silica gel chromatography (20% to 80% EtOAc/hexanes) to give a brown solid. Trituration with cold ether gives the title compound as a fine white powder. MS [ES] 577.2 (M+H)+. 1H NMR (400 MHz, CHCl3) δ 8.68 (dd, 1H, J=1.4, 4.8 Hz), 8.48 (d, 1H, J=1.8 Hz), 7.81 (s, 1H), 7.48 (m, 3H), 7.46 (m, 1H), 7.44 (m, 1H), 7.34 (m, 4H), 7.17 (m, 1H), 5.60 (s, 2H).

후처리

  1. stirringStir the resulting solution at −78° C. for 10 min.
  2. temperatureto warm to RT
  3. stirringstir for 2 h
  4. stirringstir for 30 min
  5. additionDilute
  6. washwash with water (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL)
  7. customDry
  8. filtrationfilter
  9. concentrationconcentrate the organic solution
  10. custompurify the crude material by silica gel chromatography (20% to 80% EtOAc/hexanes)
  11. customto give a brown solid

출처 및 근거

ORD 기록
ord-fd6e3dac755b431cba76f693c92ff06f
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179804B2

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