Ammonia → 6-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517946노트

반응식

HRID 517946 반응식
COCCOC[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20]#[N:21])[C:17]3[N:22]=[N:23][N:24]([CH3:25])[C:16]=3[CH:15]=2)=[CH:10][C:9]=1[C:26]([F:29])([F:28])[F:27].Cl.CCOC(C)=O.N>C1COCC1>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20]#[N:21])[C:17]3[N:22]=[N:23][N:24]([CH3:25])[C:16]=3[CH:15]=2)=[CH:10][C:9]=1[C:26]([F:29])([F:28])[F:27]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 533303896-(4-((2-Methoxyethoxy)methoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

생성물 1

HCID 1363523116-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

6-(4-((2-Methoxyethoxy)methoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (6.31 mmol, 2.57 g) was dissolved in THF (42 ml) and hydrochloric acid (2M aq) (31.5 mmol, 15.77 ml) added. The mixture was heated to 65° C. for 4 hours, after which time LCMS indicated no reaction. THF (21 ml) was added and heating continued for 16 hours then EtOAc was added and the solution basified with aqueous ammonia. Organics were separated and solvent evaporated under reduced pressure. The resulting pale yellow solid was washed with EtOAc/ether (1:1) and dried to afford product 6-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (82% yield). 1H NMR (DMSO) δ: 8.85 (s, 1H), 8.36 (s, 1H), 8.32 (d, 1H), 7.18 (d, 1H), 4.45 (s, 3H).

후처리

  1. customno reaction
  2. temperatureheating
  3. customOrganics were separated
  4. customsolvent evaporated under reduced pressure
  5. washThe resulting pale yellow solid was washed with EtOAc/ether (1:1)
  6. customdried

출처 및 근거

ORD 기록
ord-be703cf91ada48c6b984b60c9b3482a3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

반응 노트

불러오는 중…