Potassium Carbonate → HCID 178508486, compound

HRID 449034Notes

Reaction equation

HRID 449034 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]2=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[N:3]=1.[NH:25]1[CH:29]=[CH:28][C:27](B(O)O)=[N:26]1.C(=O)([O-])[O-].[K+].[K+].COCCOC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[O:18]([C:15]1[CH:16]=[CH:17][C:12]([C:4]2[N:3]=[C:2]([C:29]3[CH:28]=[CH:27][NH:26][N:25]=3)[N:6]3[CH:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=23)=[CH:13][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 18180031Water 1,2-dimethoxyethaneHCID 669155513-Bromo-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamineHCID 178514837HCID 178514837, compound

Product 1

HCID 178508486HCID 178508486, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine (20.0 mg, 0.052 mmol), 1H-pyrazol-3-yl boronic acid (6.46 mg, 0.057 mmol), Pd(PPh3)4 (10 mg, 0.01 mmol), potassium carbonate (21.8 mg, 0.157 mmol) and DME/H2O (v:v=5:1, 2 mL) was microwaved at 300 watt, 100° C. for 30 min. The solution was transferred to a 20 mL vial, and 1 mL of DMF was added. The solution was concentrated in vacuo until only DMF remained. The mixture was passed through a syringe filter pad, and prepared for Gilson HPLC separation. The fractions containing the pure product were collected and concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=6.99 (d, J=2.5 Hz, I H), 7.07-7.13 (m, 3H), 7.13-7.20 (m, 3H), 7.37-7.45 (m, 2H), 7.63-7.69 (m, 2H), 7.76 (d, J=2.5 Hz, 1H), 8.65 (br. s., 1H). MS (ES+): m/z 369.10 (100) [MH+]. HPLC: tR=20.39 min (ZQ3, polar—5 min).

Workup

  1. customwas microwaved at 300 watt, 100° C. for 30 min
  2. concentrationThe solution was concentrated in vacuo until only DMF
  3. customThe mixture was passed through a syringe
  4. filtrationfilter pad
  5. customprepared for Gilson HPLC separation
  6. additionThe fractions containing the pure product
  7. customwere collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94edacd1c69445ed8c2bca5c48810c00
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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