Diisopropylethylamine → HCID 86676330, compound

HRID 1023029Notes

Reaction equation

HRID 1023029 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].C(N(C(C)C)C(C)C)C.FC(F)(F)S(O[Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])(=O)=O.C(C1N=C(C2CCN(C(=O)CN3C(C)=CC(C(F)(F)F)=N3)CC2)SC=1)(=O)C.[CH3:62][C:63]1[N:67]([CH2:68][C:69]([N:71]2[CH2:76][CH2:75][CH:74]([C:77]3[S:78][CH:79]=[C:80]([C:82](=[N:84][O:85]CCCCC4C=CC=CC=4)[CH3:83])[N:81]=3)[CH2:73][CH2:72]2)=[O:70])[N:66]=[C:65]([C:96]([F:99])([F:98])[F:97])[CH:64]=1>ClCCl>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]([O:5][Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:27])[CH3:28])[CH2:83][C:82]([C:80]1[N:81]=[C:77]([CH:74]2[CH2:75][CH2:76][N:71]([C:69](=[O:70])[CH2:68][N:67]3[C:63]([CH3:62])=[CH:64][C:65]([C:96]([F:98])([F:99])[F:97])=[N:66]3)[CH2:72][CH2:73]2)[S:78][CH:79]=1)=[N:84][OH:85]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 1362842,6-DifluorobenzaldehydeHCID 67433897HCID 67433897, compoundHCID 86676327HCID 86676327, compound

Product 1

HCID 86676330HCID 86676330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,6-difluorobenzaldehyde (0.177 g, 1.25 mmol) in dichloromethane (5 mL) was added N-ethyl-N-(1-methylethyl)-2-propane amine (0.436 ml, 2.5 mmol) and 1,1,1-trifluoro-methanesulfonic acid, (1,1-dimethylethyl)dimethylsilyl ester (0.430 mL, 1.875 mmol). The reaction was stirred for 15 minutes and a solution of 1-[4-(4-acetyl-2-thiazolyl)-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone (i. e. the product of Example 1, Step D) (0.5 g, 1.25 mmol) dissolved in dichloromethane (2 mL) was added dropwise over 5 minutes. The resulting reaction was stirred for 6 hours and concentrated under reduced pressure. The residue was purified via silica gel chromatography (20% ethyl acetate: hexanes to 100% ethyl acetate eluant) to provide 0.62 g of the title compound.

Workup

  1. additionwas added dropwise over 5 minutes
  2. customThe resulting reaction
  3. stirringwas stirred for 6 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via silica gel chromatography (20% ethyl acetate: hexanes to 100% ethyl acetate eluant)

Sources & evidence

ORD record
ord-47b5c102185e4deaa7e2bbec05ba7f43
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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