HCID 66812902, compound → HCID 59395813, compound

HRID 1097682Notes

Reaction equation

HRID 1097682 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[CH2:14]([N:18]1[C:26]2[N:25]=[C:24]([Cl:27])[NH:23][C:22]=2[C:21](=[O:28])[N:20]([CH2:29][CH2:30][CH2:31]/[C:32](=[N:35]/[H])/[NH:33]O)[C:19]1=[O:37])[CH2:15][CH2:16][CH3:17]>CN(C=O)C>[CH2:14]([N:18]1[C:26]2[N:25]=[C:24]([Cl:27])[NH:23][C:22]=2[C:21](=[O:28])[N:20]([CH2:29][CH2:30][CH2:31][C:32]2[N:33]=[C:9]([CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[O:12][CH3:13])[O:11][N:35]=2)[C:19]1=[O:37])[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 66812902HCID 66812902, compoundHCID 178506474HCID 178506474, compound

Product 1

HCID 59395813HCID 59395813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of [3-chloro-2-(methyloxy)phenyl]acetic acid (32 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 the MDAP. The title compound was obtained as a white solid (25 mg, 28%).

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 the MDAP

Sources & evidence

ORD record
ord-576dd1bcfe594d58a28513fd1c92109b
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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