Hydrogen Bromide → HCID 67217190, compound

HRID 1969595Notes

Reaction equation

HRID 1969595 reaction equation
[CH:1]1[C:9]2[N:8]3[C:10]([C:13]45[CH2:20][CH2:19][C:16]([NH:21]C(=O)OCC6C=CC=CC=6)([CH2:17][CH2:18]4)[CH2:15][CH2:14]5)=[CH:11][N:12]=[C:7]3[CH:6]=[N:5][C:4]=2[NH:3][CH:2]=1.[BrH:32]>CCOC(C)=O>[BrH:32].[CH:1]1[C:9]2[N:8]3[C:10]([C:13]45[CH2:20][CH2:19][C:16]([NH2:21])([CH2:17][CH2:18]4)[CH2:15][CH2:14]5)=[CH:11][N:12]=[C:7]3[CH:6]=[N:5][C:4]=2[NH:3][CH:2]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67998236HCID 67998236, compound

Product 1

HCID 67217190HCID 67217190, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)bicyclo[2.2.2]octan-1-ylcarbamate (0.22 g, 0.529 mmol, prepared using Z from Preparation #N.1 and NaOH, R with diazomethane, S from Example #3, Step E, T with Lawesson's reagent and D with NaOH) was dissolved in HBr (33% in AcOH, 10 mL) and the mixture was stirred for about 10 min at ambient temperature. The reaction was then diluted with EtOAc (30 mL) and the precipitate was collected by filtration, extensively washed with MeCN and dried to yield 4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)bicyclo[2.2.2]octan-1-amine hydrobromide (0.16 g, 83%) as a yellow solid: LC/MS (Table 1, Method a) Rt=1.67 min; MS m/z 282 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washextensively washed with MeCN
  3. customdried

Sources & evidence

ORD record
ord-cb98f381c5ef458987ab9b27e6dd3f25
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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