Toluene → HCID 178522067, compound

HRID 1626767Notes

Reaction equation

C[Si]([N:5]=[N+:6]=[N-:7])(C)C.C([Sn](=O)CCCC)CCC.C1(C)C=CC=CC=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:50])[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]3[CH:41]=[CH:42][CH:43]=[C:44]4[C:49]=3[N:48]=[CH:47][CH:46]=[CH:45]4)[CH:35]=2)=[C:28]([C:51]#[N:52])[CH:27]=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:50])[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]3[CH:41]=[CH:42][CH:43]=[C:44]4[C:49]=3[N:48]=[CH:47][CH:46]=[CH:45]4)[CH:35]=2)=[C:28]([C:51]2[NH:52][N:7]=[N:6][N:5]=2)[CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

240 mg (2.08 mmol) of trimethylsilyl azide and 25.9 mg (0.10 mmol) of dibutyl tin oxide were added to a toluene (50 mL) solution comprising 400 mg (1.04 mmol) of N-(4-chloro-2-cyanophenyl)-3-(quinolin-8-yl)benzamide, and the mixture was stirred at 100° C. for 66 hours. The reaction mixture was condensed, and ethyl acetate was added thereto. Solids were collected by filtration. The obtained solids were recrystallized using DMF/IPE. The resulting solids were suspended in H2O, and stirred at 80° C. for 6 hours. Thereafter, diluted hydrochloric acid was added, and solids were collected by filtration and dried, thereby giving 242 mg of the target N-[4-chloro-2-(1H-tetrazol-5-yl)phenyl]-3-(quinolin-8-yl)benzamide (yield: 54%).

Workup

additionwas added
filtrationSolids were collected by filtration
customThe obtained solids were recrystallized
stirringstirred at 80° C. for 6 hours
additionThereafter, diluted hydrochloric acid was added
filtrationsolids were collected by filtration
customdried

Sources & evidence

ORD record: ord-e477d9575c744c1388013cd1a69f518d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785473B2

Reaction notes

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