Sodium Thiosulfate → HCID 86727639, compound

HRID 519240Notes

Reaction equation

[CH3:1][N:2]1[CH2:5][C:4]([N:7]([CH3:24])[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[C@H:12]([CH3:23])[C:13](=[O:22])[NH:14][N:15]=2)([CH3:6])[CH2:3]1.[Br-:25].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[O-]S([O-])(=S)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO>[Br:25][C:21]1[CH:20]=[C:19]2[C:10]([N:11]3[C:16]([CH2:17][O:18]2)=[N:15][NH:14][C:13](=[O:22])[C@H:12]3[CH3:23])=[CH:9][C:8]=1[N:7]([C:4]1([CH3:6])[CH2:5][N:2]([CH3:1])[CH2:3]1)[CH3:24]

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of (R)-6-[(1,3-dimethyl-azetidin-3-yl)-methyl-amino]-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (3 g, 9.11 mmol) in DCM (40 mL) and MeOH (20 mL) was added tetra-n-butylammonium tribromide (6.59 g, 13.66 mmol) in portions and the reaction mixture was stirred at 20° C. for 16 h. Saturated aqueous Na2S2O3 (10 mL) was added and saturated aqueous sodium bicarbonate (5 mL) was added to neutralize the mixture. The organic phase was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on basified silica gel (eluting with 10% MeOH in DCM) to give (R)-7-bromo-6-[(1,3-dimethyl-azetidin-3-yl)-methyl-amino]-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (3 g, 81%) as a brown solid. LC/MS (Table 1, Method 3), Rt=1.060 min.; MS m/z: 410 [M+H+2]+& 408 [M+H]+. SFC (Table 1, Method 49), Rt=5.174 min.

Workup

customThe organic phase was separated
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on basified silica gel (eluting with 10% MeOH in DCM)

Sources & evidence

ORD record: ord-8c9274b496334898be8cab8d1055aa85
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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