Triethylamine → HCID 57881563, compound

HRID 1817465Notes

Reaction equation

HRID 1817465 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:38](=[O:44])OC(Cl)(Cl)Cl)Cl.[S:46]1[CH:50]=[CH:49][N:48]=[C:47]1[C@H:51]([NH2:53])[CH3:52]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:38]([NH:53][C@@H:51]([C:47]2[S:46][CH:50]=[CH:49][N:48]=2)[CH3:52])=[O:44])=[C:18]([C:23]([F:25])([F:26])[F:24])[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 226371544-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-(trifluoromethyl)anilineHCID 42077968(αR)-α-Methyl-2-thiazolemethanamine

Product 1

HCID 57881563HCID 57881563, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-(trifluoromethyl)aniline (30 mg) was dissolved in chloroform (1 ml) and triethylamine (0.1 ml) to prepare a solution. A solution of triphosgene (35 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for one hr. Next, a solution of (1R)-1-(1,3-thiazol-2-yl)-1-ethylamine (35 mg) in chloroform (0.2 ml) was added thereto, and the mixture was stirred at room temperature for 10 hr. The stirred mixture was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (30 mg, yield 71%).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hr
  2. customThe stirred mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a6dada21a6c44024b9df5e40859d670d
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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