Trifluoroacetic acid → HCID 178509349, compound

HRID 384075Notes

Reaction equation

HRID 384075 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH2:44][CH2:45][CH2:46][NH:47]C(=O)OC(C)(C)C)[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[N:18](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:19]=[C:20]([C:21]([F:24])([F:23])[F:22])[C:13]=34)[CH:11]=2)[CH2:5][CH2:4]1)#[N:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:47][CH2:46][CH2:45][CH2:44][C:8]1[CH:7]=[C:6]([C:3]2([C:1]#[N:2])[CH2:5][CH2:4]2)[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][N:19]=[C:20]([C:21]([F:23])([F:24])[F:22])[C:13]=23)[CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67492607HCID 67492607, compound

Product 1

HCID 178509349HCID 178509349, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3-(3-(1-cyanocyclopropyl)-5-(3-(trifluoromethyl)-1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)propylcarbamate (72 mg, 0.09893 mmol) was dissolved in DCM (3 mL) and cooled to 0° C. Triethylsilane (46.01 mg, 63.20 μL, 0.3957 mmol) was added followed by TFA (0.5 mL). The reaction was stirred at 0° C. for 1 hour then the solvent removed under reduced pressure. The crude product was dissolved in DMSO and purified by FractionLynx. The fractions were passed through bicarbonate cartridges to obtain free base and lyophilised to give 1-(3-(3-aminopropyl)-5-(3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)cyclopropanecarbonitrile as a white solid (22 mg, 57%).

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe crude product was dissolved in DMSO
  3. custompurified by FractionLynx
  4. customto obtain free base

Sources & evidence

ORD record
ord-161717248c6d4db0b672dbfc9a22f372
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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