2-Aminothiazole → HCID 44552710, compound

HRID 2359398Notes

Reaction equation

HRID 2359398 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=1)[CH:10]=[CH:9]2)=[C:2]=[O:3].[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1>C1(C)C=CC=CC=1>[S:27]1[CH:28]=[CH:29][N:30]=[C:26]1[NH:25][C:2]([NH:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:22])[F:23])[CH:15]=1)[CH:10]=[CH:9]2)=[O:3]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 58154781HCID 58154781, compound

Product 1

HCID 44552710HCID 44552710, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 8-isocyanato-2-(3-(trifluoromethoxy)phenyl)quinoline (0.277 mmol) in toluene (5 mL) was added 2-aminothiazole (0.553 mmol, 55 mg). The mixture was concentrated to dryness, redissolved in pyridine and microwave heated (140° C.×10 min). The reaction mixture was diluted with CH2Cl2, washed with saturate aqueous NaHCO3, water, brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (0% to 100% ethyl acetate in pentane) afforded the desired product. MS (ESI) calcd for C20H13F3N4O2S (m/z): 430.07. found: 431 [M+1].

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionredissolved in pyridine
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. washwashed with saturate aqueous NaHCO3, water, brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (0% to 100% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-907ab84e58e04f68bf914c2c98aaff49
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

Loading…