Sodium Nitrite → HCID 58190582, compound

HRID 1892421Notes

Reaction equation

HRID 1892421 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([Br:20])=[CH:13]3)[C:5]([NH2:21])=[N:4][CH:3]=1.[N:22]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:20][C:14]1[CH:15]=[N:16][C:17]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:9][N:8]1[C:6]3=[N:7][C:2]([Br:1])=[CH:3][N:4]=[C:5]3[N:21]=[N:22]1)=[CH:19][CH:18]=2

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 58190534HCID 58190534, compound

Product 1

HCID 58190582HCID 58190582, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 6-bromo-N2-((3-bromoquinolin-6-yl)methyl)pyrazine-2,3-diamine (300 mg, 0.73 mmol) in 5 mL of acetic acid was added dropwise a solution of NaNO2 (150 mg, 2.17 mmol) in 0.5 mL of water at 20° C. The mixture was stirred at rt overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with DCM/methanol gradient to afford the title compound (130 mg, 42%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.84 (s, 1H), 8.71 (s, 1H), 8.24 (s, 1H), 8.01 (d, 1H), 7.74 (s, 2H), 5.99 (s, 2H). LCMS (method E): [MH]+=421, tR=5.50 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel eluting with DCM/methanol gradient

Sources & evidence

ORD record
ord-1510564e4c554c57aedc8b440d704304
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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