Hydrochloric Acid → HCID 86690319, compound

HRID 1521898Notes

Reaction equation

HRID 1521898 reaction equation
Br[C:2]1[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]([O:33]CC)=[O:32])[CH:3]=1.N#N.[Na].Cl.[CH3:40][OH:41]>O>[CH3:40][O:41][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[CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 947NitrogenHCID 5360545SodiumHCID 86690318HCID 86690318, compound

Product 1

HCID 86690319HCID 86690319, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising ethyl 7-(7-bromo-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (step 1)(50 mg, 0.094 mmol) in anhydrous MeOH (1 ml) was degassed with N2 and treated with sodium (10.75 mg, 0.468 mmol). After stirring at room temperature for 30 minutes, the mixture was heated to 120° C. using microwave radiation for 1 hour. The mixture was diluted with water (20 ml) and the pH was adjusted to pH1 using 2M HCl. The aqueous was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure. Purification of the crude product by chromatography on silica elutuing with 0-100% EtOAc in iso-hexane followed by 10% MeOH in EtOAc afforded the titled compound as an orange solid;

Workup

  1. temperaturethe mixture was heated to 120° C.
  2. customfor 1 hour
  3. extractionThe aqueous was extracted with DCM (×3)
  4. concentrationthe combined organic extracts were concentrated under reduced pressure
  5. customPurification of the crude product by chromatography on silica elutuing with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-e4b1e811df264a5dab65de82d981cb8a
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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