Cyclopropylamine → HCID 90038376, compound

HRID 713231Notes

Reaction equation

HRID 713231 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:8][C:7]1[N:6]=[C:5]2[CH:9]=[N:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[NH:16][CH:13]1[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazine

Product 1

HCID 90038376HCID 90038376, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,3-dichloropyrido[3,4-b]pyrazine (3.55 g, 17.75 mmol) in dioxane (71.0 mL) at room temperature was treated with cyclopropanamine (1.63 mL, 23.07 mmol), followed by dropwise addition of DIPEA (6.51 mL, 37.3 mmol). The resulting reaction mixture was stirred at room temperature for 12 h. Purification by flash silica gel chromatography using a gradient of 25% to 100% EtOAc in hexanes gave the title compound (3.15 g, 80%) as an orange solid. ESI-MS m/z [M+H]+ 221.1.

Workup

  1. customThe resulting reaction mixture
  2. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-d5574f3fc7b941cdb5cf6a8109ab2d96
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

Loading…