Water → 2'-Amino-6'-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}thio)-6-{[(2S)-2,3-dihydroxypropyl]-oxy}-3,4'-bipyridine-3',5'-dicarbonitrile

HRID 242174Notes

Reaction equation

HRID 242174 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[N:12][C:13]([O:16][CH2:17][C@@H:18]3[CH2:22][O:21]C(C)(C)[O:19]3)=[CH:14][CH:15]=2)[C:5]([C:25]#[N:26])=[C:4]([S:27][CH2:28][C:29]2[N:30]=[C:31]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[O:32][CH:33]=2)[N:3]=1.O>C(O)(=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[N:12][C:13]([O:16][CH2:17][C@@H:18]([OH:19])[CH2:22][OH:21])=[CH:14][CH:15]=2)[C:5]([C:25]#[N:26])=[C:4]([S:27][CH2:28][C:29]2[N:30]=[C:31]([C:34]3[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=3)[O:32][CH:33]=2)[N:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 685870122'-Amino-6'-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}thio)-6-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3,4'-bipyridine-3',5'-dicarbonitrile

Product 1

HCID 685870472'-Amino-6'-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}thio)-6-{[(2S)-2,3-dihydroxypropyl]-oxy}-3,4'-bipyridine-3',5'-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

95 mg (0.17 mmol) of the compound from example 32A are dissolved in 4 ml of acetic acid. 2 ml of water are then added. The reaction solution is stirred at RT for 12 h. The solvent is then removed on a rotary evaporator, and the residue is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). If required, the product may be purified further by HPLC chromatography on a chiral phase [column: Daicel Chiralpak AS 10 μm, 250 mm×20 mm; mobile phase: isohexane/ethanol 60:40 (v/v); flow rate: 15 ml/min; temperature: 40° C.; detection: 220 nm].

Workup

  1. customThe solvent is then removed on a rotary evaporator
  2. customthe residue is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  3. customthe product may be purified further by HPLC chromatography on a chiral phase [column: Daicel Chiralpak AS 10 μm, 250 mm×20 mm; mobile phase: isohexane/ethanol 60:40 (v/v); flow rate: 15 ml/min; temperature: 40° C.; detection: 220 nm]

Sources & evidence

ORD record
ord-3ed33786503b41cc9969bb5874b9b8e9
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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