Dimethyl Sulfoxide → HCID 68949280, compound

HRID 1186128Notes

Reaction equation

HRID 1186128 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-1a5bb25c8637454a932ea5bac7379589
Source dataset
uspto-grants-2014_03
Patent number
US08673895B2

Reaction notes

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