2-Furancarboxylic acid → HCID 178523861, 화합물

HRID 230377

반응식

HRID 230377 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-464fc21044f544739c16395337bedc93
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566734B2

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