Triethylamine → HCID 58527483, compound

HRID 1803384Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[N:10]2[C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=[C:13]([NH2:21])[C:12]=3[N:22]=[C:9]2[CH2:8][O:7][CH2:6]1.C(N(CC)CC)C.[C:30](Cl)(=[O:34])[CH:31]([CH3:33])[CH3:32]>C(Cl)Cl>[NH2:21][C:13]1[C:12]2[N:22]=[C:9]3[CH2:8][O:7][CH2:6][C@H:5]([CH2:4][CH2:3][CH2:2][NH:1][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[N:10]3[C:11]=2[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(11S)-11-(3-Aminopropyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (190 mg, 0.640 mmol) was dissolved in 8 mL of CH2Cl2 and the reaction mixture was cooled to 0° C. under N2. Triethylamine (356 μL, 2.56 mmol) was added followed by iso-butyryl chloride (67 μL, 0.643 mmol). After stirring overnight, the reaction mixture was diluted with 20 mL of CH2Cl2 and was washed successively with saturated NaHCO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10% methanol/CHCl3) gave a white solid. Crystallization from ethyl acetate gave N-{3-[(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propyl}-2-methylpropanamide (80 mg) as a white solid, mp 207-208° C.

Workup

washwas washed successively with saturated NaHCO3 solution, H2O and brine
dry with materialThe organic portion was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customChromatography (SiO2, 10% methanol/CHCl3) gave a white solid
customCrystallization from ethyl acetate

Sources & evidence

ORD record: ord-a3c9ca66b58e418ca426623be9cffed9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350034B2

Reaction notes

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