Sodium Bicarbonate → HCID 68699977, compound

HRID 1873560Notes

Reaction equation

HRID 1873560 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([SH:39])[N:3]=1.Cl[CH2:41][C:42]1[N:43]=[C:44]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=2)[S:45][CH:46]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][O:19][Si:20]([C:33]([CH3:35])([CH3:36])[CH3:34])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:41][C:42]2[N:43]=[C:44]([C:47]3[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=3)[S:45][CH:46]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178455535HCID 178455535, compound

Product 1

HCID 68699977HCID 68699977, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg (0.32 mmol) of the compound from Example 6A (isomer mixture) are dissolved in 2.4 ml of dry DMF, 95 mg (0.39 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 109 mg of sodium bicarbonate are added and the mixture is stirred at RT for 8 h. The mixture is then directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5), the cis/trans isomers being separated in the process.

Workup

  1. customThe mixture is then directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  2. customthe cis/trans isomers being separated in the process

Sources & evidence

ORD record
ord-93e73fa5e13b4ec2b662b1e308ecfb6e
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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