Potassium Carbonate → HCID 42603356, compound

HRID 2170545Notes

Reaction equation

HRID 2170545 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26][OH:27])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:36][CH2:37][N:38]([CH3:40])[CH3:39]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])=[C:21]([CH2:26][OH:27])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 135871486HCID 135871486, compound

Product 1

HCID 42603356HCID 42603356, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-[(3,4-dichlorophenyl)methyl]-N-[4-hydroxy-3-(hydroxymethyl)phenyl]-5-methyl-1H-1,2,3-triazole-4-carboxamide (Example 26) (0.1 g, 0.245 mmol) in DMF (10 mL), were added potassium carbonate (0.07 g, 2 eq) and (2-chloroethyl)dimethylamine hydrochloride (0.07 g, 2 eq). The reaction was heated at 40° C. for 3 days. After evaporation, the residue was diluted with DCM, washed with water and dried over sodium sulphate. After purification by flash chromatography eluting with DCM/MeOH (90/10) and recrystallisation from methanol, the title compound was obtained as a white solid (18 mg, 16%). HRMS calculated for C22H25Cl2N5O3 (M+H)+478.1413. found: 478.1435, Rt: 2.47 min. MP: 163.1° C.

Workup

  1. customAfter evaporation
  2. additionthe residue was diluted with DCM
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customAfter purification by flash chromatography
  6. washeluting with DCM/MeOH (90/10) and recrystallisation from methanol

Sources & evidence

ORD record
ord-d5e0f570aff544f79e5d8cc931951839
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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