Hydrogen Bromide → HCID 86613285, compound

HRID 1992430Notes

Reaction equation

HRID 1992430 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[N:11]=[C:12]([S:20]C)[N:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[C:14]=12.[BrH:22]>CC(O)=O>[BrH:22].[NH2:19][C:15]1[C:14]2[N:13]([C:12](=[S:20])[NH:11][C:10]=2[C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 16755043HCID 16755043, compound

Product 1

HCID 86613285HCID 86613285, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1-(1H-indol-2-yl)-3-(methylthio)imidazo[1,5-a]pyrazin-8-amine (250 mg, 0.85 mmol) in AcOH (10 mL) was treated with 48% hydrogen bromide (0.6 mL) and the mixture heated 120° C. for 24 h. The reaction mixture was then cooled and the suspended solid isolated by filtration and washed with hexane to afford 240 mg of 8-amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazine-3(2H)-thione hydrobromide. 1H NMR (400 MHz, MeOD) δ ppm 6.89 (d, J=6.06 Hz, 1H), 7.03 (s, 1H), 7.17 (tt, J=7.07, 0.76 Hz, 1H), 7.31 (tt, J=7.33, 1.01 Hz, 1H), 7.52 (dd, J=0.76 Hz, 1H), 7.63-7.76 (m, 2H); MS (ES+): m/z 282.07 [MH+].

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customthe suspended solid isolated by filtration
  3. washwashed with hexane

Sources & evidence

ORD record
ord-420983ed769d48d095a2f814a139d7e7
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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