Sodium Bicarbonate → HCID 67216338, compound

HRID 403015Notes

Reaction equation

HRID 403015 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:20]([CH3:24])([CH3:23])[O:19]3)=[CH:12][CH:11]=2)[C:5]([C:25]#[N:26])=[C:4]([SH:27])[N:3]=1.Cl[CH2:29][C:30]1[N:31]=[C:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[O:33][CH:34]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[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:20]([CH3:23])([CH3:24])[O:19]3)=[CH:12][CH:11]=2)[C:5]([C:25]#[N:26])=[C:4]([S:27][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[O:33][CH:34]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178431480HCID 178431480, compound

Product 1

HCID 67216338HCID 67216338, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 150 mg (0.39 mmol) of the compound from example 3A and 98 mg (0.43 mmol) of the compound from example 5A were suspended together with 99 mg (1.18 mmol) of sodium hydrogencarbonate in 2 ml of dry DMF. The reaction mixture was stirred at RT for 20 hours. The batch was thereafter purified directly by means of preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; eluent gradient: acetonitrile/water 10:90→95:5).

Workup

  1. customThe batch was thereafter purified directly by means of preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; eluent gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-cee4422b3dcc423693cbed09ce6c1c5f
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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