2-Fluoro-4-hydroxybenzoic Acid → HCID 136158801, compound

HRID 1097735Notes

Reaction equation

HRID 1097735 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:16]1[C:24]2[N:23]=[C:22]([Cl:25])[NH:21][C:20]=2[C:19](=[O:26])[N:18]([CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[NH:34])[NH:32]O)[C:17]1=[O:35])[CH2:13][CH2:14][CH3:15]>CS(C)=O>[CH2:12]([N:16]1[C:24]2[N:23]=[C:22]([Cl:25])[NH:21][C:20]=2[C:19](=[O:26])[N:18]([CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[N:32]=[C:4]([C:3]3[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=3[F:1])[O:6][N:34]=2)[C:17]1=[O:35])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 27833982-Fluoro-4-hydroxybenzoic AcidHCID 178448713HCID 178448713, compound

Product 1

HCID 136158801HCID 136158801, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

CDl (45 mg, 0.28 mmol) in anhydrous DMSO (0.5 ml) was added to 2-fluoro-4-hydroxybenzoic acid (40 mg, 0.25 mmol) and stirred at rt for 2 h. 5-(3-Butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (100 mg, 0.28 mmol) in DMSO (0.4 ml) was added and the resulting mixture heated at 90° C. for 18 h. Purification by MDAP afforded the title compound as a solid (38 mg, 28%).

Workup

  1. temperaturethe resulting mixture heated at 90° C. for 18 h
  2. customPurification by MDAP

Sources & evidence

ORD record
ord-a3eae9557d9e49e09fcf6bf78ff18632
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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