Dichloromethane → (S)-N-(6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-3-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl) propanamide

HRID 1043551Notes

Reaction equation

[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH:9]([NH2:13])[CH2:8][O:7]2)([O-:3])=[O:2].CCN(CC)CC.[F:21][C:22]([F:43])([F:42])[O:23][C:24]1[CH:41]=[CH:40][C:27]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][C:37](Cl)=[O:38])[CH2:31][CH2:30]2)=[CH:26][CH:25]=1.ClCCl>CN(C=O)C>[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][C@H:9]([NH:13][C:37](=[O:38])[CH2:36][CH2:35][N:32]1[CH2:31][CH2:30][CH:29]([O:28][C:27]3[CH:40]=[CH:41][C:24]([O:23][C:22]([F:21])([F:42])[F:43])=[CH:25][CH:26]=3)[CH2:34][CH2:33]1)[CH2:8][O:7]2)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Under Ar, (S)-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6-amine (110 mg, 0.6 mmol) was dissolved in DMF (6 mL), cooled to 0° C., added Et3N (0.21 mL, 2 mmol), added 3-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl) propionyl chloride (291 mg, 0.75 mmol) in batches, naturally rose to room temperature and stirred for 3 h, added an appropriate amount of dichloromethane, washed by distilled water for 3 times, followed by anhydrous sodium sulphate drying, filtrated out drying agent and spinning dry, residuals were purified by column chromatography (eluent CH2Cl2: MeOH=30:1) to give 70 mg target product, yield was 23%.

Workup

customnaturally rose to room temperature
washwashed
distillationby distilled water for 3 times
filtrationfiltrated
customout drying agent
customspinning dry
customresiduals were purified by column chromatography (eluent CH2Cl2: MeOH=30:1)
customto give 70 mg target product, yield was 23%

Sources & evidence

ORD record: ord-db94a6116aa94ef8936f50884489cfb4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563547B2

Reaction notes

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