Benzyl Bromide → HCID 16755139, compound

HRID 1992431Notes

Reaction equation

HRID 1992431 reaction equation
Br.[NH2:2][C:3]1[C:4]2[N:5]([C:9](=[S:21])[NH:10][C:11]=2[C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:7][N:8]=1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:22]([S:21][C:9]1[N:5]2[CH:6]=[CH:7][N:8]=[C:3]([NH2:2])[C:4]2=[C:11]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 86613285HCID 86613285, compound

Product 1

HCID 16755139HCID 16755139, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazine-3(2H)-thione hydrobromide (10 mg, 0.04 mmol) and benzyl bromide (5.1 uL, 0.043 mmol) in DMF (1.0 mL) was charged with N,N-diisopropylethylamine (18 uL, 0.11 mmol) and stirred at rt for 2 h. The solvent was then removed in vacuo and the crude product was dissolved in purified by preparative TLC eluting with 3% NH3/MeOH in DCM to afford 2.5 mg 3-(benzylthio)-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-8-amine. 1H NMR (400 MHz, MeOD) δ ppm 4.25 (s, 2H), 6.76 (s, 1H), 6.92 (d, J=5.05 Hz, 1H), 7.06-7.14 (m, 3H), 7.14-7.23 (m, 4H), 7.28 (d, J=5.05 Hz, 1H), 7.48(d, J=8.08 Hz, 1H), 7.63 (d, J=8.08 Hz, 1H); MS (ES+): m/z 373.35 [MH+].

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe crude product was dissolved
  3. customin purified by preparative TLC
  4. washeluting with 3% NH3/MeOH in DCM

Sources & evidence

ORD record
ord-83bd0a0e3e67484292054605154ddaa7
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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