Triethylamine → N-(5-Cyclobutyl-thiazol-2-yl)-2-quinolin-6-yl-acetamide

HRID 2085490Notes

Reaction equation

HRID 2085490 reaction equation
[CH:1]1([C:5]2[S:9][C:8]([NH2:10])=[N:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][C:29](O)=[O:30])=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)(Cl)Cl>[CH:1]1([C:5]2[S:9][C:8]([NH:10][C:29](=[O:30])[CH2:28][C:24]3[CH:23]=[C:22]4[C:27](=[CH:26][CH:25]=3)[N:18]=[CH:19][CH:20]=[CH:21]4)=[N:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 117887092-(Quinolin-6-yl)acetic acidHCID 129914235-Cyclobutyl-1,3-thiazol-2-amine

Product 1

HCID 9967013N-(5-Cyclobutyl-thiazol-2-yl)-2-quinolin-6-yl-acetamideYield 87.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-cyclobutyl-thiazol-2-ylamine (Preparation 2; 30 mg, 0.195 mmol) was treated with triethylamine (81 μl, 0.585 mmol), 6-quinolylaceticacid (40 mg, 0.214 mmol) and propylphosphonic acid cyclic anhydride (T3P, 126 mL, 0.214 mmol). After 2 hours, an additional 0.2 equiv. of T3P (22 μl) was added and the reaction was complete by TLC after 15 minutes. The reaction mixture was diluted with CHCl3, was washed with saturated aqu. NaHCO3, and was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (40:1 CHCl3—MeOH) to afford 55 mg of N-(5-cyclobutyl-thiazol-2-yl)-2-quinolin-6-yl-acetamide, the title compound, as a white solid.

Workup

  1. waitthe reaction was complete by TLC after 15 minutes
  2. washwas washed with saturated aqu
  3. dry with materialNaHCO3, and was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography (40:1 CHCl3—MeOH)

Sources & evidence

ORD record
ord-59f668edd1e0480d8dd2dea9b89de93f
Source dataset
uspto-grants-2004_04
Patent number
US06720427B2

Reaction notes

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