2,2,2-Trifluoroethyl trichloromethanesulphonate → HCID 178526825, compound

HRID 1819443Notes

Reaction equation

HRID 1819443 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.ClC(Cl)(Cl)S(O[CH2:38][C:39]([F:42])([F:41])[F:40])(=O)=O>CC#N>[N+:16]([C:15]1[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([NH:1][CH2:38][C:39]([F:42])([F:41])[F:40])[CH2:7][CH2:6]2)=[N:11][C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:30])([F:31])[F:29])=[N:13][CH:14]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 178511544HCID 178511544, compound

Product 1

HCID 178526825HCID 178526825, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (200 mg, 0.45 mmol) was suspended in CH3CN (4 mL) and cooled to 0° C. 2,2,2-Trifluoroethyl trichloromethanesulphonate (66 mg, 0.23 mmol) in CH3CN (1 mL) was added dropwise to the reaction mixture and the reaction mixture was heated to 90° C. for 5 h. The reaction mixture was concentrated and the resulting residue was diluted with ethyl acetate. The solution was treated with 1M Na2CO3 and the organic phase was separated. The aqueous phase was re-extracted with CH2Cl2. The combined organic phase was dried over Na2SO4 and concentrated. Silica gel prep TLC using 98:2 CH2Cl2:MeOH, then 7:3 Hexanes:ethyl acetate afforded 74 mg of the title compound, m/z 523.0 [M+1]+.

Workup

  1. temperaturethe reaction mixture was heated to 90° C. for 5 h
  2. concentrationThe reaction mixture was concentrated
  3. additionthe resulting residue was diluted with ethyl acetate
  4. additionThe solution was treated with 1M Na2CO3
  5. customthe organic phase was separated
  6. extractionThe aqueous phase was re-extracted with CH2Cl2
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7eae9b9d65a8441f8c1b233d87d15ef1
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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