3-Chloro-4-hydroxyphenylacetic acid → HCID 59395627, compound

HRID 1097681Notes

Reaction equation

HRID 1097681 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:13]([N:17]1[C:25]2[N:24]=[C:23]([Cl:26])[NH:22][C:21]=2[C:20](=[O:27])[N:19]([CH2:28][CH2:29][CH2:30]/[C:31](=[N:34]/[H])/[NH:32]O)[C:18]1=[O:36])[CH2:14][CH2:15][CH3:16]>CS(C)=O>[CH2:13]([N:17]1[C:25]2[N:24]=[C:23]([Cl:26])[NH:22][C:21]=2[C:20](=[O:27])[N:19]([CH2:28][CH2:29][CH2:30][C:31]2[N:32]=[C:10]([CH2:9][C:4]3[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=3)[O:12][N:34]=2)[C:18]1=[O:36])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 1185343-Chloro-4-hydroxyphenylacetic acidHCID 178506474HCID 178506474, compound

Product 1

HCID 59395627HCID 59395627, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-chloro-4-hydroxyphenylacetic acid (24 mg, 0.13 mmol) in DMSO (1 ml) was treated with CDl (21 mg, 0.13 mmol) and left to react for 30 min. (1Z)-4-(3-Butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxybutanimidamide (50 mg, 0.15 mmol) was added and the mixture heated in the microwave at 120° C. for 15 min. The solution was directly purified by MDAP to obtain the title compound as a white solid (12 mg, 17%).

Workup

  1. waitleft
  2. additionwas added
  3. customThe solution was directly purified by MDAP

Sources & evidence

ORD record
ord-5c66fc0cde9a4a4b840a03d6fabdecbf
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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