Sodium Bicarbonate → HCID 44548383, compound

HRID 1630729Notes

Reaction equation

HRID 1630729 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]#[N:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=2)[C:7]([C:22]#[N:23])=[C:6]([SH:24])[N:5]=1)[CH3:2].Cl[CH2:26][C:27]1[N:28]=[C:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[O:30][CH:31]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[O:30][CH:31]=[C:27]([CH2:26][S:24][C:6]3[C:7]([C:22]#[N:23])=[C:8]([C:12]4[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=4)[C:9]([C:10]#[N:11])=[C:4]([O:3][CH2:1][CH3:2])[N:5]=3)[N:28]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178467479HCID 178467479, compound

Product 1

HCID 44548383HCID 44548383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.293 mmol) of 2-ethoxy-4-[4-(2-hydroxyethoxy)phenyl]-6-sulphanylpyridine-3,5-dicarbonitrile together with 73 mg (0.322 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole and 98 mg (1.172 mmol) of sodium bicarbonate are stirred in 2 ml of DMF at room temperature overnight. The reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5). This gives 41.5 mg (26% of theory) of the target compound.

Workup

  1. customThe reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5)

Sources & evidence

ORD record
ord-7295aa323695455e90c52f37a41e1e7e
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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