Sodium Bicarbonate → HCID 44548708, compound

HRID 1630724Notes

Reaction equation

HRID 1630724 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[C:15]([SH:19])[N:14]=[C:13]([O:20][CH3:21])[C:12]=2[C:22]#[N:23])=[CH:7][CH:6]=1.Cl[CH2:25][C:26]1[N:27]=[C:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[O:29][CH:30]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([C:28]2[O:29][CH:30]=[C:26]([CH2:25][S:19][C:15]3[C:16]([C:17]#[N:18])=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=4)[C:12]([C:22]#[N:23])=[C:13]([O:20][CH3:21])[N:14]=3)[N:27]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178494293HCID 178494293, compound

Product 1

HCID 44548708HCID 44548708, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 mg (1.222 mmol) of 4-[4-(2-hydroxyethoxy)phenyl]-2-methoxy-6-sulphanylpyridine-3,5-dicarbonitrile together with 306 mg (1.344 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole and 410 mg (4.888 mmol) of sodium bicarbonate in 8 ml of DMF are stirred at room temperature overnight. The reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5). This gives 10.4 mg (1.6% 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-6edb1b209cde4084afeca1916b796caf
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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