Diisopropylethylamine → Tert-butyl 2-(2-((1-(cyclohexylmethyl)piperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamate

HRID 2046326ノート

反応式

HRID 2046326 の反応式
Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.[CH3:18][C:19]1[C:24]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:23]([CH3:33])[N:22]=[C:21]([O:34][CH2:35][C:36]([N:38]([CH3:45])[CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[O:37])[N:20]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:3]1([CH2:2][N:42]2[CH2:41][CH2:40][CH:39]([N:38]([CH3:45])[C:36](=[O:37])[CH2:35][O:34][C:21]3[N:20]=[C:19]([CH3:18])[C:24]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[C:23]([CH3:33])[N:22]=3)[CH2:44][CH2:43]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 137636Cyclohexane, (bromomethyl)-HCID 516892Sodium BicarbonateHCID 59336171Tert-butyl 4,6-dimethyl-2-(2-(methyl(piperidine-4-yl)amino)-2-oxoethoxy)pyrimidine-5-ylcarbamate

生成物 1

HCID 59336176Tert-butyl 2-(2-((1-(cyclohexylmethyl)piperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamate収率 46%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Bromomethyl cyclohexane (25 μL) and diisopropylethylamine (63 μL) were added to a solution of Compound 31 (71 mg) in dimethylformamide (1 mL) and the mixture was stirred at 120° C. for 8 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.; NH-DM1020) column chromatography (hexane:ethyl acetate=1:1) to give 40 mg (46% yield) of the desired product.

後処理

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.; NH-DM1020) column chromatography (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-fc51472f410e42e69ff36b929aaf972f
出典データセット
uspto-grants-2013_11
特許番号
US08592435B2

反応ノート

読み込み中…