Pyridine → HCID 178450896, compound

HRID 1486860Notes

Reaction equation

HRID 1486860 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].[OH:15][C:16]1[CH:17]=[C:18]([C:22]2[CH2:26][C:25]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[O:24][N:23]=2)[CH:19]=[CH:20][CH:21]=1.N1C=CC=CC=1.CN1C(=O)CCC1>C(#N)C>[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH2:26][C:25]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([CH2:35][C:36](=[O:37])[O:38][C:39]([CH3:42])([CH3:40])[CH3:41])[O:24][N:23]=3)[CH:17]=2)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 13387N-methyl-2-pyrrolidoneHCID 118292806Di-tert-butyl 2,2'-(3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetateHCID 178479379HCID 178479379, compound

Product 1

HCID 178450896HCID 178450896, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Carbamimidamidobenzoyl chloride hydrochloride (317 mg) was added to a mixture of di-tert-butyl 2,2′-(3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate (265 mg), pyridine (0.3 mL), and NMP (0.3 mL) at 50 C, 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 (ethyl acetate, subsequently acetonitrile/acetic acid) and then further 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 (94 mg).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate, subsequently acetonitrile/acetic acid) and
  4. additionTo the obtained fraction, a saturated aqueous solution of sodium bicarbonate was added
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3cf757473374473db41da696ade4d64a
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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