Sodium Bicarbonate → HCID 24958699, compound

HRID 1873600Notes

Reaction equation

HRID 1873600 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:20]#[N:21])=[C:18]([SH:22])[N:17]=[C:16]([NH2:23])[C:15]=2[C:24]#[N:25])[CH2:10][CH2:9]1)(=[O:3])[CH3:2].Cl[CH2:27][C:28]1[N:29]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[S:31][CH:32]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:20]#[N:21])=[C:18]([S:22][CH2:27][C:28]3[N:29]=[C:30]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[S:31][CH:32]=3)[N:17]=[C:16]([NH2:23])[C:15]=2[C:24]#[N:25])[CH2:10][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178476303HCID 178476303, compound

Product 1

HCID 24958699HCID 24958699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 mg (0.16 mmol) of the compound from Example 29A are dissolved in 3 ml of dry DMF, and 46 mg (0.19 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 53 mg (0.63 mmol) of sodium bicarbonate are added in succession. The reaction mixture is stirred at RT for 8 h. After removal of the solvent on a rotary evaporator the residue is directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. customAfter removal of the solvent
  2. customon a rotary evaporator the residue
  3. customis directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-4c4a2c512a3e4f6aac7e41fa4a98e697
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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