Dibutyltin oxide → HCID 178420277, compound

HRID 1994453Notes

Reaction equation

[CH2:1]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][CH:12]([N:17]1[C:30]3[CH:29]=[CH:28][C:27]([C:31]#[N:32])=[CH:26][C:25]=3[S:24][C:23]3[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Si]([N:37]=[N+:38]=[N-:39])(C)C.C([Sn](=O)CCCC)CCC>C(COC)OC>[CH2:1]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][CH:12]([N:17]1[C:30]3[CH:29]=[CH:28][C:27]([C:31]4[NH:39][N:38]=[N:37][N:32]=4)=[CH:26][C:25]=3[S:24][C:23]3[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenothiazine-3-carbonitrile, 2aa (10 mg, 29 μmol) in dimethoxyethane was added trimethylsilyl azide (15 μL, 115 μmol) and dibutyltin oxide (1.5 mg), and the mixture was heated in a microwave for 15 min at 150° C. The mixture was allowed to cool to rt, and purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield title compound 10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-3-(1H-tetrazol-5-yl)-10H-phenothiazine, 3aa as a TFA salt and as a mixture of endo and exo isomers. MS m/z (MH+) 481.2.

Workup

temperatureto cool to rt
custompurified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record: ord-b90169313e1046bcb4006ee107f5971b
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652005B2

Reaction notes

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