Pyridine → HCID 178451094, compound

HRID 1486899Notes

Reaction equation

HRID 1486899 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:57])[CH2:21][C:22]1([CH2:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[O:26][N:25]=[C:24]([C:27]2[CH:32]=[C:31]([OH:33])[CH:30]=[CH:29][C:28]=2[CH:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:36][CH2:35]2)[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]([CH:34]3[CH2:35][CH2:36][N:37]([CH2:40][CH2:41][C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[CH2:38][CH2:39]3)=[C:27]([C:24]3[CH2:23][C:22]([CH2:49][C:50]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:56])([CH2:21][C:20](=[O:57])[O:19][C:15]([CH3:16])([CH3:17])[CH3:18])[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 118292878tert-Butyl 3-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)propanoateHCID 178479379HCID 178479379, compound4×

Product 1

HCID 178451094HCID 178451094, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 mg) was added to a mixture of tert-butyl 3-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)propanoate (60.7 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 (23.57 mg) was further added thereto, and the obtained mixture was stirred at 50 C for 30 minutes. 4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 mg) was further added thereto, and the obtained mixture was stirred at 50 C for 30 minutes. 4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 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 (42.7 mg).

Workup

  1. stirringthe obtained mixture was stirred at 50 C for 30 minutes
  2. stirringthe obtained mixture was stirred at 50 C for 30 minutes
  3. stirringthe obtained mixture was stirred overnight at 50 C
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane, subsequently methanol/ethyl acetate)

Sources & evidence

ORD record
ord-5300887d748f4c7882a7cc4c60d30a8f
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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