Hydrogen Bromide → HCID 67216879, compound

HRID 1969596Notes

Reaction equation

HRID 1969596 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[CH2:4]1)[CH3:2].Br>CCOCC.O.C(Cl)Cl>[CH2:1]([C@H:3]1[CH2:4][NH:5][CH2:6][C@H:7]1[C:8]1[N:12]2[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=4)(=[O:21])=[O:22])[C:14]=3[N:15]=[CH:16][C:11]2=[N:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 58557844HCID 58557844, compound

Product 1

HCID 67216879HCID 67216879, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (cis)-benzyl 3-ethyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)pyrrolidine-1-carboxylate (0.838 g, 1.541 mmol, prepared using E from Example #36 Step D with TFA, N, R, S.1 with Example #3 Step E, and T with Lawesson's reagent) was added a solution of HBr (2.50 mL, 15.19 mmol, 33% in acetic acid). The reaction mixture was stirred at ambient temperature for about 1 h. The reaction was diluted with Et2O (50 mL) and water (20 mL). The layers were stirred for about 3 min and the organic layer was decanted then the procedure was repeated 5 times. The aqueous layer was cooled to about 0° C. was basified with saturated aqueous NaHCO3 solution (10 mL) to about pH 7. The aqueous layer was extracted with EtOAc (3×50 mL), combined, and dried over anhydrous Na2SO4, filtered and concd to give a brown solid. The solid was dissolved in DCM (50 mL) and washed with water (3×20 mL), dried over anhydrous Na2SO4, filtered and coned to afford 8-((cis)-4-ethylpyrrolidin-3-yl)-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.453, 61%) as a brown residue: LC/MS (Table 1, Method a) Rt=1.73 min; MS m/z: 410 (M+H)+.

Workup

  1. stirringThe layers were stirred for about 3 min
  2. customthe organic layer was decanted
  3. temperatureThe aqueous layer was cooled to about 0° C.
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customto give a brown solid
  8. washwashed with water (3×20 mL)
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered

Sources & evidence

ORD record
ord-a8e6aa80e0dd41028b543886cc28f6af
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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