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

HRID 517946ノート

反応式

HRID 517946 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-be703cf91ada48c6b984b60c9b3482a3
出典データセット
uspto-grants-2015_08
特許番号
US09115126B2

反応ノート

読み込み中…