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

HRID 403017Notes

Reaction equation

HRID 403017 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@@H:18]3[CH2:22][O:21]C(C)(C)[O:19]3)=[CH:12][CH:11]=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]=[CH: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 666718892-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 666718012-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(2S)-2,3-dihydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An amount of 400 mg (0.70 mmol) of the compound from example 7A was introduced in 17 ml of acetic acid and then admixed cautiously with 8.6 ml of water. The batch was stirred at RT for 12 hours. After the reaction mixture had been concentrated on a rotary evaporator, the residue was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; eluent gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gave the product as a white solid.

Workup

  1. concentrationAfter the reaction mixture had been concentrated on a rotary evaporator
  2. customthe residue was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; eluent gradient: acetonitrile/water 10:90→95:5)
  3. customRemoval of the solvent
  4. customon a rotary evaporator

Sources & evidence

ORD record
ord-0a8f942a8dca4c47b539ef232fe95a17
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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