Hydrochloric Acid → N-(2-amino-5-(thiophen-2-yl)phenyl)isobutyramide

HRID 2201678

反応式

HRID 2201678 の反応式
[C:1]([NH:6][C:7]1[CH:12]=[C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[CH:9][C:8]=1[NH:18]C(=O)OC(C)(C)C)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.O1CCOCC1>CO>[NH2:18][C:8]1[CH:9]=[CH:10][C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:12][C:7]=1[NH:6][C:1](=[O:5])[CH:2]([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71007313Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate

生成物 1

HCID 86712519N-(2-amino-5-(thiophen-2-yl)phenyl)isobutyramide収率 36%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate (0.2 g, 0.52 mmol) in methanol (4 mL) was added 4M HCl in Dioxane (2 mL, 0.53 mmol, 1 equiv.) at 0° C. The reaction was warmed to room temperature and stirred for 2 h. After completion the reaction was concentrated under reduced pressure then basified with a saturated aqueous solution of NaHCO3. The obtained solid was filtered and dried. The crude material was purified by column chromatography (silica gel, MeOH/CH2Cl2) to afford N-(2-amino-5-(thiophen-2-yl)phenyl)isobutyramide (0.05 mg, 36% yield). ESI+ MS: m/z 261 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 9.10 (s, 1H0, 7.5 (s, 1H0, 7.34 (d, J=4.5 Hz, 1H), 7.23-7.19 (m, 2H), 7.05-7.03 (m, 1H0, 6.75 (d, J=8.5 hz, 1H0, 5.03 (s, 2H), 2.67-2.64 (m, 1H), 1.13 (d, J=7 Hz, 6H).

後処理

  1. concentrationAfter completion the reaction was concentrated under reduced pressure
  2. filtrationThe obtained solid was filtered
  3. customdried
  4. customThe crude material was purified by column chromatography (silica gel, MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-3c7f963030f04dcfa4b7039870522207
出典データセット
uspto-grants-2016_06
特許番号
US09365498B2

関連ノート

読み込み中…