Trifluoroacetic acid → HCID 178481282, compound

HRID 539916Notes

Reaction equation

HRID 539916 reaction equation
[F:1][C:2]1[C:3]([NH:36][C@H:37]2[CH2:42][CH2:41][CH2:40][C@@H:39]([NH:43][C:44]([C:46]3[N:47]=[CH:48][N:49]([CH3:51])[CH:50]=3)=[O:45])[CH2:38]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[N:6][CH:7]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[C:3]([NH:36][C@H:37]2[CH2:42][CH2:41][CH2:40][C@@H:39]([NH:43][C:44]([C:46]3[N:47]=[CH:48][N:49]([CH3:51])[CH:50]=3)=[O:45])[CH2:38]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86707190HCID 86707190, compound

Product 1

HCID 178481282HCID 178481282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[(1R,3S)-3-[[5-fluoro-2-(1-tritylpyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]-1-methyl-imidazole-4-carboxamide, 25, (0.235 g, 0.347 mmol) in dichloromethane (6.90 mL) at room temperature was added Et3SiH (1.661 mL, 10.40 mmol) followed by TFA (0.401 mL, 5.200 mmol). The reaction mixture was stirred for 1 hour. The mixture was diluted with dichloromethane and quenched with aqueous saturated Na2CO3 solution. The organic phase was extracted with ethyl acetate, washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by silica chromatography (0-7% MeOH [2N NH3] in ethyl acetate) to give the desired product: LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=1.46 min (M+H)=436.62.

Workup

  1. customquenched with aqueous saturated Na2CO3 solution
  2. extractionThe organic phase was extracted with ethyl acetate
  3. washwashed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by silica chromatography (0-7% MeOH [2N NH3] in ethyl acetate)

Sources & evidence

ORD record
ord-9be73a008d6948f0af24d244dcd885c4
Source dataset
uspto-grants-2014_10
Patent number
US08871774B2

Reaction notes

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