Chloroacetaldehyde → 4-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol

HRID 2075665Notes

Reaction equation

HRID 2075665 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([S:18][C:19]3[CH:20]=[C:21]([C:25]4(C#N)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)=[CH:7][CH:8]=2)[N:3]=1.Cl[CH2:34][CH:35]=O.[O:37]1CCOCC1>O.C([O-])(O)=O.[Na+]>[C:12]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([S:18][C:19]4[CH:20]=[C:21]([C:25]5([OH:37])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)=[CH:7][CH:8]=3)[N:3]3[CH:34]=[CH:35][N:1]=[C:2]3[CH:11]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 33ChloroacetaldehydeHCID 312751,4-DioxaneHCID 670910914-[3-(2-Amino-4-phenyl-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 248757664-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 1t (78 mg, 0.18 mmol) in 1,4-dioxane (3 mL) and water (1 mL) was added chloroacetaldehyde (50 wt %, 0.04 mL, 0.27 mmol) and saturated aqueous NaHCO3 (2 drops), and the reaction was heated to 70° C. until no starting material was seen by tlc analysis. The mixture was concentrated and purified by preparative HPLC to give the desired product, 1u.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9cedc9dd10ab4bbcbe56d69391f3d249
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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