Chlorotrimethylsilane → 6-Chloro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide hydrochloride

HRID 589867Notes

Reaction equation

HRID 589867 reaction equation
[C:1]([C:4]1[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:6]([Cl:20])[N:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C:8]=12)(=[O:3])[NH2:2].Cl[Si](C)(C)C>ClCCl.CO>[ClH:20].[Cl:20][C:6]1[N:7]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]2=[C:4]([C:1]([NH2:2])=[O:3])[C:5]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 66584861tert-butyl 8-carbamoyl-6-chloro-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

Product 1

HCID 867625676-Chloro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide hydrochlorideYield 196.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution cooled to about 0° C. of 5.99 g (15.9 mmol) of tert-butyl 8-carbamoyl-6-chloro-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate in 50 ml of dichloromethane and 200 ml of methanol are added portionwise 12.6 g (116 mmol) of chlorotrimethylsilane. The mixture is stirred for 16 hours at room temperature and the reaction medium is then concentrated under reduced pressure and co-evaporated twice with ethyl acetate. The residue is crystallized from ethyl acetate to give 4.88 g of 6-chloro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide hydrochloride in the form of a white solid after drying at 60° C. under reduced pressure.

Workup

  1. concentrationthe reaction medium is then concentrated under reduced pressure
  2. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b62d372a1e0847b1b9d308ac92fa1bf9
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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