Dibutyltin oxide → HCID 46189889, compound

HRID 390417Notes

Reaction equation

[C:1]([S:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH:18]=[C:17]([CH2:19][C:20]#[N:21])[CH:16]=[N:15]1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N:33]=[N+:34]=[N-:35])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([S:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH:18]=[C:17]([CH2:19][C:20]2[N:33]=[N:34][NH:35][N:21]=2)[CH:16]=[N:15]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To N-[3-tert-butylsulfanylmethyl-4-(4-cyanomethyl-pyrazol-1-ylmethyl)-phenyl]-2,2-dimethyl-propionamide (0.015 g, 0.04 mmol) in toluene (1 mL) was added trimethylsilyl azide (0.02 mL, 0.1 mmol), followed by dibutyltin oxide (0.001 g, 0.004 mmol), and the reaction was stirred at 80° C. overnight. Starting material was still present, so additional trimethylsilyl azide (0.20 mL, 1.1 mmol) and dibutyltin oxide (0.005 g, 0.02 mmol) were added, and the reaction was stirred for 6 hours at 100° C. After work-up, the crude material was purified by preparative HPLC to give the title compound.

Workup

stirringthe reaction was stirred for 6 hours at 100° C
customAfter work-up, the crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-9fa5aa9ec2634330adfcf22a1ee57b3d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383654B2

Reaction notes

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