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

HRID 1959673Notes

Reaction equation

HRID 1959673 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-09c64756d2224ef1b876af7da6474434
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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