Diisopropylethylamine → Tert-butyl 3-[(6-amino-5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate

HRID 444838ノート

反応式

HRID 444838 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[C:18](Cl)[N:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C.O>[NH2:15][C:16]1[N:17]=[C:18]([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[CH:19]=[CH:20][C:21]=1[C:22]#[N:23]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 5458091-BOC-3-AminopiperidineHCID 203116862-Amino-6-chloropyridine-3-carbonitrile

生成物 1

HCID 57911735Tert-butyl 3-[(6-amino-5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

2.15 g (10.7 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 1.50 g (9.77 mmol) of 2-amino-6-chloropyridine-3-carbonitrile (Example 28A) and 1.89 g (14.7 mmol) of diisopropylethylamine were suspended in 6 ml of DMSO and heated in a microwave reactor at 130° C. for 8 h. The reaction mixture was diluted with ethyl acetate (100 ml) and water (40 ml), and the organic phase was separated off and washed with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1 to 1:1). This gave 2.04 g (60% of theory) of the product as a solid.

後処理

  1. customthe organic phase was separated off
  2. washwashed with saturated aqueous sodium chloride solution (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1 to 1:1)

出典と根拠

ORDレコード
ord-7a31d3b9d4ff4565979b615fef97de39
出典データセット
uspto-grants-2013_07
特許番号
US08476267B2

反応ノート

読み込み中…