Ammonium Chloride → HCID 118159233, compound

HRID 713258Notes

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([NH2:17])[CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>>[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:17][CH:13]1[CH2:16][CH2:15][CH2:14]1

Participants

Reactant 4

HCID 25517Ammonium Chloride

HCID 75645Cyclobutylamine

HCID 81531Diisopropylethylamine

HCID 231227312,3-Dichloropyrido[3,4-b]pyrazine

Product 1

HCID 118159233HCID 118159233, compoundYield 99%

Conditions

Temperature: 0 °C

Procedure

A mixture of 2,3-dichloropyrido[3,4-b]pyrazine (100 mg, 0.500 mmol), cyclobutanamine (47.0 μL, 0.550 mmol) and DIPEA (260 μL, 1.500 mmol) was stirred at 0° C. for 15 min then at rt for 30 min. Saturated aqueous NH4Cl was added to the mixture and the product was extracted with EtOAc. The combined organic layers were filtered through a pad of silica (EtOAc wash) and the filtrate was concentrated to afford 3-chloro-N-cyclobutylpyrido[3,4-b]pyrazin-2-amine (116.1 mg, 99%) as a yellow solid, which was used without further purification. ESI-MS m/z [M+H]+ 235.2.

Workup

waitat rt for 30 min
extractionthe product was extracted with EtOAc
filtrationThe combined organic layers were filtered through a pad of silica (EtOAc wash)
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-376e9a34aeed4177b9489f1e54a2aa30
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181249B2

Reaction notes

Loading…