Sodium Bicarbonate → HCID 135926275, compound

HRID 1630731Notes

Reaction equation

HRID 1630731 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]#[N:15])=[C:12]([SH:16])[N:11]=[C:10]([O:17][CH3:18])[C:9]=2[C:19]#[N:20])=[CH:4][CH:3]=1.Cl[CH2:22][C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[O:26][CH:27]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:25]2[O:26][CH:27]=[C:23]([CH2:22][S:16][C:12]3[C:13]([C:14]#[N:15])=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=4)[C:9]([C:19]#[N:20])=[C:10]([O:17][CH3:18])[N:11]=3)[N:24]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178494291HCID 178494291, compound

Product 1

HCID 135926275HCID 135926275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

64 mg (0.224 mmol) of 4-(4-hydroxyphenyl)-2-methoxy-6-sulphanylpyridine-3,5-dicarbonitrile together with 88 mg (0.269 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole and 57 mg (0.672 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, with 0.1% TFA added). This gives 44 mg (41% of theory) of the target compound.

Workup

  1. customThe reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added)

Sources & evidence

ORD record
ord-c02350d9be2e40e4ae39687a367652be
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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