Triethylamine → [5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-carbamic acid 1-(3-trifluoromethyl-phenyl)-ethyl ester

HRID 631915노트

반응식

HRID 631915 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])=CC=1.[F:41][C:42]([F:53])([F:52])[C:43]1[CH:44]=[C:45]([CH:49]([OH:51])[CH3:50])[CH:46]=[CH:47][CH:48]=1>C1(C)C=CC=CC=1>[F:41][C:42]([F:52])([F:53])[C:43]1[CH:44]=[C:45]([CH:49]([O:51][C:22](=[O:31])[NH:19][C:9]2[N:10]([CH3:13])[N:11]=[N:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH3:50])[CH:46]=[CH:47][CH:48]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 1362961-(3-(Trifluoromethyl)phenyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 712662515-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid

생성물 1

HCID 118062436[5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-carbamic acid 1-(3-trifluoromethyl-phenyl)-ethyl ester수율 81.4%

시약·촉매·용매 1

HCID 1140Toluene용매3회

실험 절차

5-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid (from step 4a in Example 1, 517 mg, 1.83 mmol) was suspended in 10 mL of toluene. Triethylamine (0.27 mL) was added followed by DPPA (530 mg, 1.92 mmol) in toluene (2 mL). The mixture was stirred for 10 minutes. 3-Trifluoromethylphenylethanol (383 mg, 2.02 mmol) in toluene (2 mL) was added. The mixture was stirred at 85° C. for 3 hrs. The mixture was extracted with ethyl acetate and water. The organic layer was washed with brine and dried. Solvents were evaporated and the residue was purified by ISCO flash column chromatography (0% to 50% ethyl acetate in hexanes, 40 g silica gel) to give [5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-carbamic acid 1-(3-trifluoromethyl-phenyl)-ethyl ester as an amorphous fluffy white powder (700 mg, 81.4% yield). LC/MS calcd for C19H16BrF3N4O2 (m/e) 468.0, obsd 468.9 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.35-1.70 (br, 3H), 3.85 (s, 3H), 5.85 (br, 1H), 7.30-7.90 (m, 8H), 10.01 (br s, 1H).

후처리

  1. stirringThe mixture was stirred at 85° C. for 3 hrs
  2. extractionThe mixture was extracted with ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. customSolvents were evaporated
  6. customthe residue was purified by ISCO flash column chromatography (0% to 50% ethyl acetate in hexanes, 40 g silica gel)

출처 및 근거

ORD 기록
ord-ac151bc6a37f4a0397ed928a7c1ea146
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321738B2

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