Dimethyl Sulfoxide → 3-(4-Bromo-phenylsulfanyl)-1-(8-fluoro-2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazin-8-ylamine

HRID 1992435Notes

Reaction equation

HRID 1992435 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8](=[S:28])[NH:9][C:10]=2[C:11]2[C:20]([F:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.F[B-](F)(F)F.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([N+]#N)=[CH:37][CH:36]=1.CS(C)=O>C(Cl)Cl>[Br:34][C:35]1[CH:40]=[CH:39][C:38]([S:28][C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[C:20]([F:21])=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:18]4)=[CH:13][CH:12]=3)[N:9]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 2734810Benzenediazonium, 4-bromo-, tetrafluoroborate(1-) (1:1)HCID 167536808-Amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazine-3-thiol

Product 1

HCID 167536793-(4-Bromo-phenylsulfanyl)-1-(8-fluoro-2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazin-8-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a round bottom flask was added 8-amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-2H-imidazo[1,5-a]pyrazine-3-thione (21 mg, 0.000053 mol), 4-bromobenzenediazonium tetrafluoroborate (0.018 g, 0.000064 mol) and dimethyl sulfoxide (0.1 mL, 0.002 mol) and the reaction mixture was stirred in ice for 30 min. The reaction mixture was cooled, dissolved in DCM and washed with water. Purification by Gilson HPLC eluting with 10→90% acetonitrile: H2O afforded the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=7.13-7.17 (m, 2H), 7.23 (d, J=5.05 Hz, 1H), 7.42 (d, J=8.59 Hz, 2H), 7.49-7.59 (m, 3H), 7.61 (d, J=5.05 Hz, 1H), 7.75-7.78 (m, 2H), 8.05 (d, J=8.59 Hz, 1H), 8.22-8.27 (m, 2H), 8.32 (dd, J=8.72, 1.39 Hz, 1H). MS (ES+): m/z 544.15 (100)[MH+]. HPLC: tR=2.69 min (Open Lynx polar—5 min).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. customPurification by Gilson HPLC
  4. washeluting with 10→90% acetonitrile

Sources & evidence

ORD record
ord-6f75fc8ef95841bb8ed91d0cb34d7214
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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