1,3-Dichloroacetone → HCID 86624337, compound

HRID 2362826Notes

Reaction equation

HRID 2362826 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1)#[N:2].Cl[CH2:14][C:15]([CH2:17]Cl)=O.[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[CH:30][CH:29]=2)[C:23]([C:40]#[N:41])=[C:22]([SH:42])[N:21]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[CH:32][CH:33]=2)[C:23]([C:40]#[N:41])=[C:22]([S:42][CH2:17][C:15]2[N:12]=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[S:11][CH:14]=2)[N:21]=1

Participants

6

Reactant 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 2757973(4-Cyanophenyl)thioureaHCID 178483863HCID 178483863, compound

Product 1

HCID 86624337HCID 86624337, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 26.6 mg (0.15 mmol) of N-(4-cyanophenyl)thiourea and 19 mg (0.15 mmol) of 1,3-dichloroacetone in 0.4 ml of DMF is stirred at +80° C. for 3 h. After cooling to RT, a solution of 50.9 mg (0.15 mmol) of the compound from Example 34A in 0.2 ml of DMF and 50 mg (0.6 mmol) of sodium bicarbonate are added. The mixture is then stirred at RT for 12 h. The reaction mixture is filtered and purified directly by preparative HPLC (column: Macherey Nagel VP50/21 Nucleosil 100-5 C18 Nautilus, 5 μm, 21 mm×50 mm; wavelength: 220 nm; flow rate: 25 ml/min; mobile phase A=water+0.1% formic acid, mobile phase B=acetonitrile; gradient: 0 min 10% B→2 min 10% B→6 min 90% B→7 min 90% B→7.1 min 10% B→8 min 10% B). The product-containing fractions are combined and concentrated using a rotary evaporator.

Workup

  1. filtrationThe reaction mixture is filtered
  2. custompurified directly by preparative HPLC (column: Macherey Nagel VP50/21 Nucleosil 100-5 C18 Nautilus, 5 μm, 21 mm×50 mm; wavelength: 220 nm; flow rate: 25 ml/min; mobile phase A=water+0.1% formic acid, mobile phase B=acetonitrile; gradient: 0 min 10% B→2 min 10% B→6 min 90% B→7 min 90% B→7.1 min 10% B→8 min 10% B)
  3. concentrationconcentrated
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-11ea1f95a082427d8b7a97265932a502
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

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