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

HRID 456164Notes

Reaction equation

HRID 456164 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]=1NC.Br[C:15]1[C:16]([NH2:22])=[N:17][CH:18]=[C:19]([Br:21])[N:20]=1.C[CH2:24][N:25](C(C)C)C(C)C>C(Cl)Cl.O>[Br:21][C:19]1[N:20]=[C:15]([NH:25][CH2:24][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 66927191HCID 66927191, compound

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 N-(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 in a microwave to 120° C. for 10 hour. The reaction was diluted with DCM and water. The organic layer was washed with NH4Cl (aq.), 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. washThe organic layer was washed with NH4Cl (aq.)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography (DCM:MeOH)

Sources & evidence

ORD record
ord-d81b734fe9a84050be5c22f92e1810e6
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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