Diisopropylethylamine → 5-Bromo-N*3*-(7-fluoro-quinolin-6-ylmethyl)-pyrazine-2,3-diamine

HRID 1892335Notes

Reaction equation

HRID 1892335 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][NH2:13].Br[C:15]1[C:16]([NH2:22])=[N:17][CH:18]=[C:19]([Br:21])[N:20]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[Br:21][C:19]1[N:20]=[C:15]([NH:13][CH2:12][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:2]=2[F:1])[N:9]=[CH:8][CH:7]=[CH:6]3)[C:16]([NH2:22])=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 52987914(7-Fluoroquinolin-6-yl)methanamine

Product 1

HCID 593417825-Bromo-N*3*-(7-fluoro-quinolin-6-ylmethyl)-pyrazine-2,3-diamineYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of C-(7-fluoro-quinolin-6-yl)-methylamine (1.69 g, 9.63 mmol), 3,5-dibromopyrazin-2-amine (2.43 g, 9.63 mmol) and DIPEA (2.96 g, 22.90 mmol) was heated with microwave irradiation at 120° C. for 10 h. The reaction mixture was diluted with DCM and water. The organic layer was separated and washed with saturated NH4Cl solution, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (DCM:MeOH) to give the title compound as a yellow solid (2.60 g, 69%). LCMS (method E): [MH]+=348/350, tR=5.21 min.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated NH4Cl solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (DCM:MeOH)

Sources & evidence

ORD record
ord-e5722f5ad4224a1c8534eb45aa0ffd7e
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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