Triethylamine → 3-chloro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-amine

HRID 454888Notes

Reaction equation

C(N(CC)CC)C.Cl.[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N:19]1[CH2:22][CH:21]([NH2:23])[CH2:20]1.[Cl:24][C:25]1[C:30](Cl)=[N:29][CH:28]=[CH:27][N:26]=1>CN(C=O)C.O>[Cl:24][C:25]1[C:30]([NH:23][CH:21]2[CH2:20][N:19]([C:10]3[CH:11]=[CH:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]=3)[CH2:22]2)=[N:29][CH:28]=[CH:27][N:26]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Triethylamine (560 mg, 5.6 mmol), 1-(quinolin-2-yl)azetidin-3-amine hydrochloride (557 mg, 2.8 mmol) and 2,3-dichloro-pyrazine (414 mg, 2.8 mmol) were dissolved in DMF (20 mL). The resulting mixture was heated to 90° C. overnight. The mixture was then diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were combined and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether) to give 3-chloro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-amine (479 mg, 1.5 mmol, 55% yield) as white solid. ESI-MS (M+1): 312 calc. for C16H14ClN5 311.

Workup

extractionextracted with EtOAc (2×50 mL)
washwashed with water (20 mL) and brine (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customThe filtrate was evaporated in vacuo
customthe residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-ab0ae19450eb41ed9f32bcac1a7f1554
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497265B2

Reaction notes

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