Imidazole → HCID 178456842, compound

HRID 1989844Notes

Reaction equation

HRID 1989844 reaction equation
[CH:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:19]=[C:18]([OH:20])[C:17]3[C:12](=[CH:13][C:14]([OH:21])=[CH:15][CH:16]=3)[N:11]=2)[N:9]=1)([CH3:3])[CH3:2].[CH3:22][CH:23]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH3:24].N1C=CN=C1>CN(C=O)C>[CH:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:19]=[C:18]([OH:20])[C:17]3[C:12](=[CH:13][C:14]([O:21][Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:24])[CH3:22])=[CH:15][CH:16]=3)[N:11]=2)[N:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 178456838HCID 178456838, compound

Product 1

HCID 178456842HCID 178456842, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-Isopropylamino-thiazol-4-yl)-quinoline-4,7-diol (1.27 g, 4.2 mmol) in 4 mL of DMF was added TIPSCl (2.67 mL, 12.6 mmol) followed by imidazole (2.86 g, 42 mmol). The solution was stirred for 5 min at rt, dissolved in 20 mL EtOAC, quenched by saturated solution of NH4Cl in H2O. The solution was extracted and evaporated under vacuo. The crude product was purified by silica gel chromatography using SiO2 (eluted with 5% to 20% MeOH/DCM) to give 2-(2-Isopropylamino-thiazol-4-yl)-7-triisopropylsilanyloxy-quinolin-4-ol as a dark orange solid (1.9 g, 99%). 1H-NMR (300 MHz, DMSO): δ 11.0 (bs, 1H), 7.93 (d, 1H), 7.70 (bs, 1H), 7.42 (s, 1H), 7.25 (s, 1H), 6.81 (dd, 1H), 6.49 (s, 1H), 3.97-3.87 (m, 1H), 1.38-1.25 (m, 1H), 1.22 (d, 6H), 1.07 (d, 6H).

Workup

  1. dissolutiondissolved in 20 mL EtOAC
  2. customquenched by saturated solution of NH4Cl in H2O
  3. extractionThe solution was extracted
  4. customevaporated under vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1c7e86127dc34215ade33f440565874c
Source dataset
uspto-grants-2010_01
Patent number
US07642339B2

Reaction notes

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