2-Furancarboxylic acid → HCID 178523861, compound

HRID 230377

Reaction equation

HRID 230377 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 178523861HCID 178523861, compoundYield 94%

Conditions

Temperature
22 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-464fc21044f544739c16395337bedc93
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Linked notes

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