1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-tert-Butyl-3-(2-chloro-benzyl)-7-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 2173522Notes

Reaction equation

HRID 2173522 reaction equation
[C:1]([C:5]1[N:6]=[C:7](Cl)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[O:23]=[S:24]1(=[O:29])[CH2:28][CH2:27][CH2:26][NH:25]1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:1]([C:5]1[N:6]=[C:7]([N:25]2[CH2:26][CH2:27][CH2:28][S:24]2(=[O:29])=[O:23])[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6421571,3-PropanesultamHCID 866832845-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 866832905-tert-Butyl-3-(2-chloro-benzyl)-7-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidineYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (15.9 mg, 47.2 μmol), 1,1-dioxo-isothiazolidine (11.4 mg, 94.4 μmol) and DBU (14.2 μL, 94.4 mmol) in DMF (250 μL) was stirred at the room temperature overnight. The reaction mixture was directly purified by preparative HPLC (column: Gemini 5 um C18 110A 75×30 mm. mobile phase: water (0.05% Et3N): acetonitrile 75:25% to 5:95%. WL: 230 nm Flow: 30 mL/min.) to afford the title compound as white solid (3.10 mg, 16%). MS(m/e): 387.3 (MH+).

Workup

  1. customThe reaction mixture was directly purified by preparative HPLC (column: Gemini 5 um C18 110A 75×30 mm. mobile phase: water (0.05% Et3N): acetonitrile 75:25% to 5:95%. WL: 230 nm Flow: 30 mL/min.)

Sources & evidence

ORD record
ord-1dba48ed07fd427a85d83824ecd33963
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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