3-Fluoro-4-hydroxybenzeneacetic acid → HCID 59395574, compound

HRID 1097683Notes

Reaction equation

HRID 1097683 reaction equation
[F: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]>CN(C=O)C>[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]([F: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 680143-Fluoro-4-hydroxybenzeneacetic acidHCID 178506474HCID 178506474, compound

Product 1

HCID 59395574HCID 59395574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (3-fluoro-4-hydroxyphenyl)acetic acid (27 mg, 0.16 mmol) in DMF (1.5 ml) was treated with CDl (26 mg, 0.16 mmol) and left to react for 45 min. (1Z)-4-(3-Butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxybutanimidamide (60 mg, 0.18 mmol) was added and the mixture heated in the microwave at 140° C. for 15 min. After cooling, the reaction was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated then concentrated and purified by MDAP. The title compound was obtained as a white solid (10 mg, 12%).

Workup

  1. additionwas treated with CDl (26 mg, 0.16 mmol)
  2. waitleft
  3. additionwas added
  4. temperatureAfter cooling
  5. customthe reaction was partitioned between 2M HCl (aq) and EtOAc
  6. customThe organic layer was separated
  7. concentrationthen concentrated
  8. custompurified by MDAP

Sources & evidence

ORD record
ord-a9ad18856c974c42aa23775260d5c673
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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