Potassium Carbonate → 6-(1-Benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519019Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[NH2:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[O:18][CH2:17][C:16]1[N:11]2[CH:12]([CH3:23])[C:13](=[O:22])[NH:14][N:15]=1.CS(O[C:29]1([CH3:46])[CH2:32][N:31]([CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30]1)(=O)=O>CC(O)C>[CH:33]([N:31]1[CH2:32][C:29]([NH:7][C:8]2[CH:9]=[C:10]3[C:19](=[CH:20][CH:21]=2)[O:18][CH2:17][C:16]2[N:11]3[CH:12]([CH3:23])[C:13](=[O:22])[NH:14][N:15]=2)([CH3:46])[CH2:30]1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of K2CO3 (0.238 g, 1.722 mmol), 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #2, Step E, 0.20 g, 0.861 mmol), and 1-benzhydryl-3-methylazetidin-3-yl methanesulfonate (Preparation #3, Step B, 0.428 g, 1.292 mmol) in propan-2-ol (10 ml) was stirred at 80° C. overnight. The solution was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0 to 50% EtOAc in petroleum ether) to give 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.234 g, 58%). LC/MS (Table 1, Method 2) Rt=0.948 min; MS m/z: 468 [M+H]+.

Workup

concentrationThe solution was concentrated in vacuo
customthe residue was purified by column chromatography on silica gel (eluting with 0 to 50% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-bb21ea5509434e35be58ce1cd5b8d1fa
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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