Pyridine → HCID 178450898, compound

HRID 1486910Notes

Reaction equation

HRID 1486910 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].[C:15]([O:19][C:20](=[O:54])[CH2:21][C:22]1([CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[O:26][N:25]=[C:24]([C:27]2[CH:32]=[C:31]([OH:33])[CH:30]=[CH:29][C:28]=2[CH2:34][CH2:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])[CH2:23]1)([CH3:18])([CH3:17])[CH3:16].N1C=CC=CC=1.CN1C(=O)CCC1>C(#N)C>[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:33][C:31]2[CH:30]=[CH:29][C:28]([CH2:34][CH2:35][C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])=[C:27]([C:24]3[CH2:23][C:22]([CH2:46][C:47]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:53])([CH2:21][C:20](=[O:54])[O:19][C:15]([CH3:18])([CH3:16])[CH3:17])[O:26][N:25]=3)[CH:32]=2)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 13387N-methyl-2-pyrrolidoneHCID 118292778HCID 118292778, compoundHCID 178479379HCID 178479379, compound2×

Product 1

HCID 178450898HCID 178450898, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Carbamimidamidobenzoyl chloride hydrochloride (96 mg) was added to a mixture of benzyl 3-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoate (227 mg), pyridine (0.2 mL), and NMP (0.2 mL) at 50 C, and the obtained mixture was stirred at 50 C for 30 minutes. 4-Carbamimidamidobenzoyl chloride hydrochloride (96 mg) was further added thereto, and the obtained mixture was stirred overnight at 50 C. To the reaction mixture, acetonitrile was added. The precipitate was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane, subsequently methanol/ethyl acetate) to obtain the title compound (163 mg).

Workup

  1. stirringthe obtained mixture was stirred overnight at 50 C
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane, subsequently methanol/ethyl acetate)

Sources & evidence

ORD record
ord-dfcdb8371db64e1c9c7f0b91237250a6
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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