Chloroform → HCID 67273297, compound

HRID 602262Notes

Reaction equation

HRID 602262 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][C@@H:13]([CH3:16])[CH2:14][OH:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.N1C=C[CH:21]=[CH:20][CH:19]=1.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:20]([C:21]1[N:12]([C@@H:13]([CH3:16])[CH2:14][OH:15])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:19]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10176127Pyridinium chlorideHCID 67274034HCID 67274034, compound

Product 1

HCID 67273297HCID 67273297, compoundYield 609.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of (2S)-2-[(3-aminoquinolin-4-yl)amino]propan-1-ol (0.98 g, 4.49 mmol) in 50 mL of toluene was treated with triethyl orthopropioate (1.1 mL, 5.39 mmol) and pyridine HCl (52 mg, 0.45 mmol), and heated to 90° C. under an atmosphere of N2. After ˜20 hours, the reaction was allowed to cool back to ambient temperature and the solvent was removed under reduced pressure to give an orange solid. Chromatography (AFC, SiO2, 20-40% CMA/CHCl3) gave (2S)-2-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol (0.70 g) as a white solid.

Workup

  1. temperatureto cool back to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. customto give an orange solid

Sources & evidence

ORD record
ord-ef0fdfce235545c0b604f41dc4d007dd
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

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