2-Furancarboxylic acid → HCID 178523861, 화합물

HRID 23366

반응식

HRID 23366 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:21][C@H:22]([C:33]1[NH:34][CH:35]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:37]=1)[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:21][C@H:22]([C:33]1[NH:34][CH:35]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:37]=1)[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:8]

참가 물질

4

반응물 3

HCID 69192-Furancarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 178511781HCID 178511781, 화합물

생성물 1

HCID 178523861HCID 178523861, 화합물수율 94%

반응 조건

온도
22 °C

실험 절차

2-Furancarboxylic acid (12.6 mg, 0.11 mmol) was activated overnight at about 22° C. with carbonyldiimidazole (0.11 mmol, 0.2M in chloroform). 2-{(1S)-1-Amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole (0.1 mmol, 0.5M in chloroform) was added to the media and the mixture was stirred for about 12 hours at about 22° C. Aminomethylated resin was then added (50-60 mg, 1.2 mmol/g, Novabiochem) in order to quench the excess of acylating agent for about 12 hours. Purification on silica gel pad (200 mg, Alltech) with ethyl acetate as eluent gave the expected product (37.2 mg, 94%). 1H-NMR (CDCl3, 100 MHz) δ: 8.36 (br s, 1H); 7.67-6.4 (m, 16H); 5.48 (qd, J=7.1 Hz, 1H); 3.6 (ABX system, 2H). LC/MS: m/z=397 (M+H).

후처리

  1. additionAminomethylated resin was then added (50-60 mg, 1.2 mmol/g, Novabiochem) in order
  2. customto quench the excess
  3. customfor about 12 hours
  4. customPurification on silica gel pad (200 mg, Alltech) with ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-53c35be4278545ed89106e250fee70d4
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852725B1

연결된 노트

불러오는 중…