Cyclopropylamine → HCID 90038223, compound

HRID 713261Notes

Reaction equation

HRID 713261 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[C:5]2=[N:6][C:7]=1[Cl:8].[CH:14]1([NH2:17])[CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:8][C:7]1[N:6]=[C:5]2[C:9]([CH3:13])=[N:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[NH:17][CH:14]1[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 118159190HCID 118159190, compound

Product 1

HCID 90038223HCID 90038223, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,3-Dichloro-5-methylpyrido[3,4-b]pyrazine (1.700 g, 7.94 mmol) was added to dioxane (15.88 mL), then cyclopropanamine (0.864 mL, 12.71 mmol) and DIPEA (2.24 mL, 13.50 mmol) were added sequentially. The mixture was stirred for 12 h at room temperature then concentrated under reduced pressure. Column chromatography using a gradient of 10% to 75% EtOAc in hexanes provided 3-chloro-N-cyclopropyl-5-methylpyrido[3,4-b]pyrazin-2-amine (1.3 g) as a brown solid.

Workup

  1. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f61abd1cb3f410abdc59e800d5f5208
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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