1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178452348、化合物

HRID 1909049

反応式

HRID 1909049 の反応式
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CCN(C(C)C)C(C)C.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C>[C:16]([O:15][C:13]([N:20]1[CH2:25][CH2:24][N:23]([C:10]([C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)=[O:12])[CH2:22][CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 4594565-Benzimidazolecarboxylic acid

生成物 1

HCID 178452348HCID 178452348、化合物収率 35.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
23 °C

実験手順

In a 250 mL round bottom flask with a stirbar was added Benzimidazole-5-carboxylic acid (2.00 g, 12.3 mmol), Boc-piperazine (2.41 g, 13.0 mmol, 1.05 eq), and Hunig's Base (3.78 mL, 27.1 mmol, 2.2 eq) in DMF (35 mL). After 5 minutes 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.60 g, 13.6 mmol, 1.1 eq) was added portion wise and the dark solution stirred for 2 hr at 23° C. The reaction was diluted with Ethyl Acetate (250 mL) and partitioned between water (50 mL). The layers were separated and the organic washed with water (2×50 mL), brine (30 mL), dried (Na2SO4), and concentrated to a dark oil. The reaction was purified using Biotage MPLC system (40M column size, 0-20% Methanol/CH2Cl2 over 35 Column Volumes) giving the desired product as a beige solid (1.45 g, 4.39 mmol, 35.6%). 1H NMR (DMSO-d6, 400 MHz) δ 12.6 (s, 1H), δ 8.31 (s, 1H), δ 7.66-7.60 (m, 2H), δ 7.25 (bs, 1H), δ 3.60-3.25 (m, 8H), δ 1.40 (s, 9H); LRMS (m/z): 353 (M+Na), 331 (M+H), 275.

後処理

  1. custompartitioned between water (50 mL)
  2. customThe layers were separated
  3. washthe organic washed with water (2×50 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a dark oil
  6. customThe reaction was purified

出典と根拠

ORDレコード
ord-ac23c4d182ab49559c8f9d7891055846
出典データセット
uspto-grants-2013_12
特許番号
US08598217B2

関連ノート

読み込み中…