HCID 86690333, compound → HCID 86690332, compound

HRID 1428683Notes

Reaction equation

HRID 1428683 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:9]=2)[N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:3]1=[O:34]>C1COCC1>[O:34]=[C:3]1[N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:5]2=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:9]=[C:10]2[CH2:2]1

Participants

3

Reactant 1

HCID 86690333HCID 86690333, compound2×

Product 1

HCID 86690332HCID 86690332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(7,7-Dibromo-6-oxo-2,3-di-p-tolyl-6,7-dihydro-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoic acid (mixture from step 1) (127 mg, 0.211 mmol) in dry THF (5 ml) under nitrogen was treated with 10% Pd(C) (22.48 mg, 0.021 mmol) and the mixture was stirred at RT under an atmosphere of hydrogen for 16 hours. The resulting mixture was filtered through Celite® and washed through with DCM. The filtrate was concentrated under reduced pressure and purification was carried out by chromatography on silica eluting with 0-100% EtOAc in iso-hexane. Further purification was carried out by dissolving the product in DCM (minimal) and loading onto a 20 cm×20 cm preparative TLC plate. The plate was run using a solvent system of 75% EtOAc in iso-hexane (300 ml) and the appropriate strip of Si was scrapped off the plate. The silica was suspended in 10% MeOH/DCM and sonicated. The suspension was filtered, rinsing the solid with 10% MeOH/DCM. The filtrate was concentrated under reduced pressure to afford the title compound;

Workup

  1. filtrationThe resulting mixture was filtered through Celite®
  2. washwashed through with DCM
  3. concentrationThe filtrate was concentrated under reduced pressure and purification
  4. customFurther purification
  5. dissolutionby dissolving the product in DCM (minimal)
  6. customsonicated
  7. filtrationThe suspension was filtered
  8. washrinsing the solid with 10% MeOH/DCM
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0eb3c6956f6d4850ad37a7a18034f4d8
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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