Ammonia → 2-Pentylthiazolo[4,5-c]quinolin-4-amine

HRID 857979Notes

Reaction equation

HRID 857979 reaction equation
[CH2:1]([C:6]1[S:7][C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH:18]C(=O)C(Cl)(Cl)Cl)[C:9]=2[N:25]=1)[CH2:2][CH2:3][CH2:4][CH3:5].N.ClCCl>CO>[CH2:1]([C:6]1[S:7][C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:18])[C:9]=2[N:25]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6344DichloromethaneHCID 22648316HCID 22648316, compound

Product 1

HCID 98383452-Pentylthiazolo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trichloroacetyl isocyanate (0.51 mL) was added to a solution of 2-pentylthiazolo[4,5-c]quinoline-5N-oxide (0.78 g) in dichloromethane (50 mL). The reaction mixture was stirred at ambient temperature for about 75 minutes and then concentrated under vacuum to provide crude N-(2-pentylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide. The amide was combined with a solution of ammonia in methanol (40 mL of 2M). Dichloromethane was added to bring all of the material into solution. When the reaction was completed as indicated by thin layer chromatography, the reaction mixture was concentrated under vacuum. The residue was mixed with dichloromethane and sodium bicarbonate. The organic layer was separated, washed with sodium bicarbonate then with water, dried over magnesium sulfate and then concentrated under vacuum to provide a white solid. This material was recrystallized from ethyl acetate to provide 2-pentylthiazolo[4,5-c]quinolin-4-amine as an off-white crystalline solid, m.p. 119–121° C. Analysis: Calculated for C15H17N3S: % C, 66.39; % H, 6.31; % N, 15.48; Found: % C, 66.21; % H, 6.35; % N, 15.39.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. additionThe residue was mixed with dichloromethane and sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with sodium bicarbonate
  5. dry with materialwith water, dried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customto provide a white solid
  8. customThis material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-672844a6fc6845ad9e390e45cc6ab260
Source dataset
uspto-grants-2006_12
Patent number
US07148232B2

Reaction notes

Loading…