Pyridine → HCID 178450902, compound

HRID 1486876Notes

Reaction equation

HRID 1486876 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:47])[CH2:21][C:22]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[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][CH2:37][CH2:36][CH2:35]2)[CH2:23]1)([CH3:18])([CH3:17])[CH3:16].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O.C(#N)C.CN1C(=O)CCC1>[C:15]([O:19][C:20](=[O:47])[CH2:21][C:22]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[O:26][N:25]=[C:24]([C:27]2[CH:32]=[C:31]([O:33][C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([NH:2][C:3]([NH2:5])=[NH:4])=[CH:14][CH:13]=3)[CH:30]=[CH:29][C:28]=2[CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[CH2:23]1)([CH3:17])([CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 118292862tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(2-cyclohexyl-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylateHCID 178479379HCID 178479379, compound

Product 1

HCID 178450902HCID 178450902, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

4-Carbamimidamidobenzoyl chloride hydrochloride (55.1 mg) was added to a mixture of tert-butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(2-cyclohexyl-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (54.1 mg), pyridine (0.06 mL), and NMP (0.06 mL) at 50 C, and the obtained mixture was stirred at 50 C for 5 days. The reaction mixture was fractionated by HPLC (C18, mobile phase: water/acetonitrile (system containing 0.1% TFA)). To the obtained fraction, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (12.7 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0a7c6153ed464d148413d661d89b8458
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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