Hydrochloric Acid → HCID 86690312, compound

HRID 1428660Notes

Reaction equation

HRID 1428660 reaction equation
[CH:1]1([C:4]2[NH:26][C:7]3=[N:8][C:9]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[N:11]=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1.N#N.[H-].[Na+].Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].Cl>CN(C=O)C.O>[CH:1]1([C:4]2[N:26]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:7]3=[N:8][C:9]([C:19]4[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[N:11]=[C:6]3[CH:5]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 86690311HCID 86690311, compound

Product 1

HCID 86690312HCID 86690312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Cyclopropyl-2,3-di-p-p-tolyl-5H-pyrrolo[2,3-b]pyrazine (step 5) (189 mg, 0.557 mmol) in anhydrous DMF (3 ml) degassed with N2 was treated with NaH (60% in mineral oil) (24.50 mg, 0.612 mmol). After stirring at RT for 30 minutes, ethyl 7-bromoheptanoate (0.119 ml, 0.612 mmol) was added and stirring continued for 2 hours. The mixture was diluted with water (50 ml) and the pH was adjusted to pH 1 using 2M HCl. The resulting mixture was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure. Purification of the crude product by chromatography on silica eluting with 0-10% EtOAc in iso-hexane afforded the titled compound as a yellow oil;

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. extractionThe resulting mixture 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 eluting with 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-b63b5a47dc5544cebfd8f0fb048d5be9
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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