Benzylamine → HCID 71143763, compound

HRID 510171Notes

Reaction equation

HRID 510171 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[N:9]=2)[N:4](S(C2C=CC(C)=CC=2)(=O)=O)[CH:3]=1.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=C3[C:49]=2[O:50]C2C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=2C3(C)C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].O1CCOCC1>[CH2:33]([NH:40][C:49]([C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([S:17]([CH:20]([CH3:21])[CH3:22])(=[O:19])=[O:18])=[CH:15][CH:16]=3)[N:9]=2)[NH:4][CH:3]=1)=[O:50])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 667631397-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

Product 1

HCID 71143763HCID 71143763, compoundYield 128%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

7-iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine (100 mg, 0.3 mmol), benzylamine (160.7 mg, 1.5 mmol), (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (9.5 mg, 0.016 mmol), palladium diacetate (3.7 mg, 0.016 mmol) and sodium carbonate (70 mg, 0.65 mmol) were added to dioxane (2 mL) in a sealed flask. The reaction was flushed well with carbon monoxide and heated to 60° C. overnight. 2M aqueous LiOH (2 mL) was added and the resultant mixture stirred overnight, then the volatile components were stripped under a stream of nitrogen gas at 60° C. and the solid residue taken up in DMSO (2 mL). This solution was filtered and then purified by FractionLynx mass directed HPLC, then freeze dried to give N-benzyl-2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (8.9 mg, 15%). 1H NMR (400.0 MHz, DMSO) δ 12.94 (d, J=2.5 Hz, 1H), 9.13 (s, 1H), 8.68 (t, J=5.8 Hz, 1H), 8.54 (d, J=3.1 Hz, 1H), 8.41 (d, J=8.5 Hz, 2H), 7.94 (d, J=8.5 Hz, 2H), 7.46 (d, J=7.2 Hz, 2H), 7.41-7.37 (m, 2H), 7.30 (t, J=7.3 Hz, 1H), 7.30 (s, 1H), 4.67 (d, J=5.7 Hz, 1H), 3.51 (t, J=6.8 Hz, 1H) and 1.21 (d, J=6.9 Hz, 6H) ppm; MS (ES+) 435.2.

Workup

  1. customThe reaction was flushed well with carbon monoxide
  2. addition2M aqueous LiOH (2 mL) was added
  3. customwere stripped under a stream of nitrogen gas at 60° C.
  4. filtrationThis solution was filtered
  5. custompurified by FractionLynx mass
  6. customfreeze dried

Sources & evidence

ORD record
ord-c8d7b29288bb4d5eaf286d5bfa8545fc
Source dataset
uspto-grants-2015_08
Patent number
US09096602B2

Reaction notes

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