Water → HCID 86690331, compound

HRID 1428680Notes

Reaction equation

HRID 1428680 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[NH:29][C:10]2=[N:11][C:12]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:14]=[C:9]2[CH:8]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].O>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[N:29]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[C:10]2=[N:11][C:12]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:14]=[C:9]2[CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 86690329HCID 86690329, compound

Product 1

HCID 86690331HCID 86690331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2,3-Dip-tolyl-5H-pyrrolo[2,3-b]pyrazin-6-yl)ethyl acetate (step 3) (12 mg, 0.031 mmol) was dissolved in dry DMF (1 ml) at RT and treated with K2CO3 (12.91 mg, 0.093 mmol) and ethyl 7-bromoheptanoate (0.012 ml, 0.062 mmol). The resulting brown suspension was stirred at RT for 16 hours. The mixture was then heated at 60° C. for 5 hours and after cooling to RT, stirred overnight. The mixture was added to water (30 ml) and extracted with DCM (×3). The combined organic extracts were passed through a phase separating column and concentrated under reduced pressure to afford the title compound;

Workup

  1. temperatureThe mixture was then heated at 60° C. for 5 hours
  2. temperatureafter cooling to RT
  3. stirringstirred overnight
  4. extractionextracted with DCM (×3)
  5. customseparating column
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f83e47fd0c449e390e17cc3159b5643
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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