4,N-Dihydroxy-benzamidine → HCID 136158797, compound

HRID 1097706Notes

Reaction equation

HRID 1097706 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[C:6](=[O:19])[N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:4]=2[N:3]=1.O[NH:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[NH:28]>CN(C=O)C>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[O:18][N:28]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=4)[N:26]=3)[C:6](=[O:19])[N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 51497564,N-Dihydroxy-benzamidineHCID 59405408HCID 59405408, compound

Product 1

HCID 136158797HCID 136158797, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoic acid (50 mg, 0.14 mmol) in DMF (2 ml) was treated with CDl (23 mg, 0.14 mmol) and stirred at rt for 30 min. N,4-dihydroxybenzenecarboximidamide (26 mg, 0.17 mmol) was added and the mixture heated in the microwave at 120° C. for 15 min. After cooling the reaction was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, concentrated and purified by the MDAP. The title compound was obtained as an off-white solid (17 mg, 26%).

Workup

  1. temperaturethe mixture heated in the microwave at 120° C. for 15 min
  2. temperatureAfter cooling the reaction
  3. customwas partitioned between 2M HCl (aq) and EtOAc
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. custompurified by the MDAP

Sources & evidence

ORD record
ord-002477aaf245455f8674956b1b0c2f7c
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

Loading…