Chloroform → (11S)-11-Isopropyl-3-(2-morpholin-4-ylethoxy)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 221619Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH:19]([CH3:21])[CH3:20])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][C:6]([OH:22])=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(Cl)(Cl)Cl>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH:19]([C@@H:15]1[N:14]2[C:10]3[C:9]4[C:4](=[CH:5][C:6]([O:22][CH2:31][CH2:32][N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[CH:7][CH:8]=4)[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[CH2:18][O:17][CH2:16]1)([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of (11S)-6-amino-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-3-ol (0.30 g, 1.0 mmol) dissolved in 5 mL of DMF was treated with cesium carbonate (1.0 g, 3.0 mmol) and tetrabutylammonium bromide (0.30 g, 1.0 mmol) and a solution of 4-(2-chloroethyl)morpholine hydrochloride (0.21 g, 1.1 mmol). After stirring for 18 hours at 65° C., the reaction mixture was concentrated under reduced pressure to give a solid. The solid was dissolved in CH2Cl2 (100 mL) and washed with H2O (100 mL). The organic layer was concentrated under reduced pressure to give a solid. Chromatography (SiO2, 0-15% CMA/CHCl3) gave a white solid which was crystallized from acetonitrile to give 110 mg of the title compound as white, mp 194-195° C.

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
customto give a solid
washwashed with H2O (100 mL)
concentrationThe organic layer was concentrated under reduced pressure
customto give a solid
customwas crystallized from acetonitrile

Sources & evidence

ORD record: ord-d9d3f57310254f799a6ba4c9b6ce6ba0
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207162B2

Reaction notes

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