Diisopropylethylamine → HCID 72706904、化合物

HRID 1750276ノート

反応式

HRID 1750276 の反応式
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:19][C@@H:20]1[O:25][CH2:24][CH2:23][NH:22][CH2:21]1.C(N(CC)C(C)C)(C)C>C(O)CCC>[CH3:19][C@@H:20]1[O:25][CH2:24][CH2:23][N:22]([C:2]2[C:3]3[C:10]([C:11]4[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=4)[C:14]#[N:15])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:21]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 36689624(2S)-2-MethylmorpholineHCID 867069533-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile

生成物 1

HCID 72706904HCID 72706904、化合物

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile (C14) (100 mg, 0.393 mmol) and (2S)-2-methylmorpholine (54 mg, 0.53 mmol) in n-butanol (20 mL) was added N,N-diisopropylethylamine (152 mg, 1.18 mol), and the reaction mixture was heated at 100° C. for 18 hours. The reaction mixture was then concentrated in vacuo; purification via preparative HPLC (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 27% to 47% B) provided the product as a white solid. Yield: 17.5 mg, 54.8 μmol, 14%. LCMS m/z 320.2 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 10.71 (br s, 1H), 8.53 (br s, 1H), 7.73-7.89 (m, 2H), 7.51-7.69 (m, 2H), 7.28 (s, 1H, assumed; partially obscured by solvent peak), 3.56-3.77 (m, 3H), 3.39-3.54 (m, 2H), 2.86-2.98 (m, 1H), 2.53-2.65 (m, 1H), 0.93-1.03 (m, 3H).

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurification via preparative HPLC (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 27% to 47% B)

出典と根拠

ORDレコード
ord-42f5e3ad0aef4bd7b3ba9812b54f992c
出典データセット
uspto-grants-2015_10
特許番号
US09156845B2

反応ノート

読み込み中…