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

HRID 2201678

반응식

HRID 2201678 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3c7f963030f04dcfa4b7039870522207
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365498B2

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