Lithium Chloride → 5-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897405ノート

反応式

HRID 897405 の反応式
Cl[C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[C:4]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=2)[N:3]=1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH:39]=[C:38](OS(C(F)(F)F)(=O)=O)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].[Cl-].[Li+].C[Sn](C)C.C[Sn](C)C.[F-].[K+]>O1CCOCC1.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]([O:32][C:33]([N:35]1[CH2:36][CH:37]=[C:38]([C:2]2[N:7]3[CH:8]=[N:9][N:10]=[C:6]3[C:5]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[C:4]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=3)[N:3]=2)[CH2:39][CH2:40]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

参加物

8

反応物 5

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 6327618HexamethylditinHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 223466035-Chloro-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

生成物 1

HCID 223465805-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

試薬・触媒・溶媒 2

HCID 178420554HCID 178420554、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

5-Chloro-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine (2.0 g, 5.0 mmol), 1-(t-butoxycarbonyl)-4-(trifluoromethyl sulfonyloxy)-1,2,3,6-tetrahydropyridine (2.0 g, 6.0 mmol), lithium chloride (6.64 g, 15.0 mmol), hexamethylditin (2.0 g, 6.0 mmol) and tetrakistriphenylphosphinopalladium (0.3 g, 0.25 mmol) were combined in dioxane (25 ml) and the resulting solution was heated to 90° C. for 18 hours. The mixture was added to aq. KF and was stirred for 2 hours and then partitioned with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated to a syrup. Purification by column chromatography on silica gel (30% ethyl acetate in hexane) gave the product as a syrup; MS m/z (M+H)+ 557.2; C27H24F3ClN6O2 require 556.2.

後処理

  1. custompartitioned with methylene chloride
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a syrup
  5. customPurification by column chromatography on silica gel (30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-dc929cbb45904f4a900e43af13b3a269
出典データセット
uspto-grants-2005_07
特許番号
US06921762B2

反応ノート

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