Potassium Carbonate → HCID 86690327, compound

HRID 1428692Notes

Reaction equation

HRID 1428692 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH:11]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[NH:9][C:5]2=[N:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].[Cl-].[NH4+]>CN(C=O)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][N:9]1[C:5]2=[N:6][C:7]([Cl:8])=[C:2]([Br:1])[N:3]=[C:4]2[CH:11]=[C:10]1[CH:12]1[CH2:14][CH2:13]1)[CH3:32]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 122490Ethyl 7-bromoheptanoateHCID 86690340HCID 86690340, compound

Product 1

HCID 86690327HCID 86690327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-3-chloro-6-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine (step 1) (1.0 g, 3.696 mmol) in DMF (10 ml), cooled to 0° C. and degassed with argon, was treated with potassium carbonate (1.53 g, 10.88 mmol) and stirred for 5 minutes. The reaction mixture was then treated with ethyl 7-bromoheptanoate (960 mg, 4.066 mmol) and stirred at room temperature for 16 hours. Saturated aqueous ammonium chloride solution was added slowly at 0° C. and the mixture was extracted with diethyl ether. The organic portion was dried (Na2SO4), and the solvent was removed under reduced pressure. Purification of the crude product by chromatography on neutral alumina eluting with 0-2% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. customdegassed with argon
  2. stirringstirred at room temperature for 16 hours
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the crude product by chromatography on neutral alumina eluting with 0-2% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-622463b987d24c7884764653a77f3335
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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