Pyridine → HCID 178451063, compound

HRID 1486870Notes

Reaction equation

HRID 1486870 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:59])[CH2:21][C:22]1([CH2:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[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]([C:40](=[O:50])[CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[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]([C:40](=[O:50])[CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])[CH2:38][CH2:39]3)=[C:27]([C:24]3[CH2:23][C:22]([CH2:51][C:52]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:58])([CH2:21][C:20](=[O:59])[O:19][C:15]([CH3:17])([CH3:18])[CH3:16])[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 118292794tert-Butyl 4-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)-4-oxobutanoateHCID 178479379HCID 178479379, compound5×

Product 1

HCID 178451063HCID 178451063, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Carbamimidamidobenzoyl chloride hydrochloride (12.99 mg) was added to a mixture of tert-butyl 4-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)-4-oxobutanoate (35.0 mg), pyridine (0.1 mL), and NMP (0.1 mL) at 50 C, and the obtained mixture was stirred at 50 C for 10 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (12.99 mg) was added thereto, and the obtained mixture was stirred at 50 C for 10 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (12.99 mg) was added thereto, and the obtained mixture was stirred at 50 C for 10 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (12.99 mg) was added thereto, and the obtained mixture was stirred at 50 C for 10 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (12.99 mg) was added thereto, and the obtained mixture was stirred overnight at 50 C. To the reaction mixture, acetonitrile was added, and the obtained mixture was purified by silica gel column chromatography (NH, ethyl acetate/hexane, subsequently methanol/ethyl acetate) to obtain the title compound (29.2 mg).

Workup

  1. stirringthe obtained mixture was stirred at 50 C for 10 minutes
  2. stirringthe obtained mixture was stirred at 50 C for 10 minutes
  3. stirringthe obtained mixture was stirred at 50 C for 10 minutes
  4. stirringthe obtained mixture was stirred overnight at 50 C
  5. customthe obtained mixture was purified by silica gel column chromatography (NH, ethyl acetate/hexane, subsequently methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6fec6cfdcfb346709b1e3a164e6ae637
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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