Cyclohexyl bromide → Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

HRID 2370910ノート

反応式

HRID 2370910 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Br[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.CC(=O)OCC.O>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 7960Cyclohexyl bromideHCID 8471TriethylamineHCID 22728543Water ethylacetateHCID 178470993HCID 178470993、化合物

生成物 1

HCID 11544682Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate収率 22.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 60.1 mg (0.23 mmol) of the compound from example 1g, 37.7 mg (0.23 mmol) of bromocyclohexane and 100 μl of triethylamine in 1 ml of absolute THF was treated in a microwave at 170° C. for 40 min. The reaction solution was then taken up in a little EA/water (1:1), and the phases were separated off, dried over Na2SO4, filtered and evaporated to dryness. Purification by chromatography on RP silica gel with CH3CN/water/0.1% TFA as mobile phase and freeze-drying of the combined product fractions afforded 18.0 mg of the desired compound as bistrifluoroacetate in the form of an amorphous solid.

後処理

  1. customthe phases were separated off
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customPurification by chromatography on RP silica gel with CH3CN/water/0.1% TFA as mobile phase
  6. customfreeze-drying of the combined product fractions

出典と根拠

ORDレコード
ord-13de9d4c20a745ad8e4286c2483a3358
出典データセット
uspto-grants-2014_04
特許番号
US08710232B2

反応ノート

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