4,N-Dihydroxy-benzamidine → HCID 136158802, compound

HRID 1097709Notes

Reaction equation

HRID 1097709 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].O[NH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)=[NH:27]>CN(C=O)C>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[O:22][N:27]=[C:26]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[N:25]=2)[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 51497564,N-Dihydroxy-benzamidineHCID 59395495HCID 59395495, compound

Product 1

HCID 136158802HCID 136158802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoic acid (100 mg, 0.29 mmol) in DMF (4 ml) was treated with CDl (52 mg, 0.32 mmol). After 1 h, N,4-dihydroxybenzenecarboximidamide was added and the mixture heated at 100° C. for 6 h. On cooling, the reaction mixture was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated. Purification by MDAP afforded the title compound as a pale grey solid (72 mg).

Workup

  1. temperatureOn cooling
  2. customthe reaction mixture was partitioned between 2M HCl (aq) and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by MDAP

Sources & evidence

ORD record
ord-d0d455ab64b64c13bf12bea200a9504f
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

Loading…