Sodium Bicarbonate → HCID 89265164, compound

HRID 1873569Notes

Reaction equation

HRID 1873569 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[C:5]([C:23]#[N:24])=[C:4]([SH:25])[N:3]=1.Cl[CH2:27][C:28]1[N:29]=[C:30]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[S:31][CH:32]=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][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][CH2:11]2)[C:5]([C:23]#[N:24])=[C:4]([S:25][CH2:27][C:28]2[N:29]=[C:30]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[S:31][CH:32]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 82179814HCID 82179814, compoundHCID 178451764HCID 178451764, compound

Product 1

HCID 89265164HCID 89265164, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.20 mmol) of the compound from Example 17A (70% pure) and 130 mg (0.24 mmol) of 4-(chloromethyl)-N-(4-fluorophenyl)-1,3-thiazole-2-amine (from 4-fluorophenylthiourea and 1,3-dichloroacetone) are dissolved in 2.5 ml of dry DMF, and 100 mg (0.98 mmol) of sodium bicarbonate are added. The reaction mixture is stirred at RT for 8 h. After filtration the filtrate is concentrated under reduced pressure and the residue that remains is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. filtrationAfter filtration the filtrate
  2. concentrationis concentrated under reduced pressure
  3. customthe residue that remains is 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-e41377c547f74fbcbaf71ed5ff47eefe
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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