Dimethyl Sulfoxide → HCID 68949280, compound

HRID 1485359Notes

Reaction equation

HRID 1485359 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15](OS(C(F)(F)F)(=O)=O)=[N:16][C:17]([S:19][CH3:20])=[N:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[F:29][C:30]([F:39])([F:38])[C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1.CS(C)=O>O>[CH3:20][S:19][C:17]1[N:16]=[C:15]([NH:35][C:34]2[CH:36]=[CH:37][C:31]([C:30]([F:29])([F:38])[F:39])=[CH:32][CH:33]=2)[C:12]2[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=2[N:18]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 99644-(Trifluoromethyl)anilineHCID 86718473HCID 86718473, compound

Product 1

HCID 68949280HCID 68949280, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing methylsulfanyl-4-trifluoromethanesulfonyloxy-5,6,8,9-tetrahydro-pyrimido[4,5-d]azepine-7-carboxylic acid tert-butyl ester (950 mg, 2.15 mmol), 4-trifluoromethylaniline (0.6 mL, 4.74 mmol) and DMSO (8 mL) was heated at 100° C. for 24 h. The reaction mixture was cooled to rt and diluted with water and extracted with EtOAc. The combined organic extracts were dried and concentrated. The residue was purified (FCC; MeOH/CH2Cl2) to give the title compound (422 mg, 55%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified (FCC; MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a3eb5697eaf14573bf3e330df97de734
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

Loading…