Procaine → HCID 11684261, compound

HRID 229324Notes

Reaction equation

HRID 229324 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[CH2:16][CH2:15][CH2:14]4)[C:6]=2[N:7]=1.[CH2:20]([N:22]([CH2:35][CH3:36])[CH2:23][CH2:24][O:25][C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1)[CH3:21].FC(F)(F)C([O-])=O>CS(C)=O>[CH2:35]([N:22]([CH2:20][CH3:21])[CH2:23][CH2:24][O:25][C:26](=[O:34])[C:27]1[CH:28]=[CH:29][C:30]([NH:33][C:2]2[N:3]=[CH:4][C:5]3[N:10]=[N:9][N:8]([C:11]4[CH:12]=[C:13]5[C:17](=[CH:18][CH:19]=4)[CH2:16][CH2:15][CH2:14]5)[C:6]=3[N:7]=2)=[CH:31][CH:32]=1)[CH3:36]

Participants

5

Reactant 3

HCID 4914ProcaineHCID 84468TrifluoroacetateHCID 57757710HCID 57757710, compound

Product 1

HCID 11684261HCID 11684261, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3) (40 mg, 0.15 mmol) in DMSO (1.6 mL) was added 2-(diethylamino)ethyl-4-aminobenzoate (38 mg, 0.16 mmol). The mixture was irradiated at 140° C. for 10 min. After cooling to room temperature, the mixture was purified by reverse-phase chromatography to furnish the desired product (4) (32.2 mg, 0.046 mmol) as a trifluoroacetate salt. MS calcd. for C26H30N7O2 m/z calcd 472.24 (M+H),+ found 472.24.

Workup

  1. customThe mixture was irradiated at 140° C. for 10 min
  2. customthe mixture was purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-d110e523b79c43bca3f8a42453fe5157
Source dataset
uspto-grants-2009_07
Patent number
US07563781B2

Reaction notes

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