Trifluoroacetic acid → HCID 54588864, compound

HRID 1396171Notes

Reaction equation

HRID 1396171 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH:10][C:11]3[N:16]=[C:15]([F:17])[C:14]([CH:18]([C:20]4[C:28]5[C:27]([O:29][CH3:30])=[N:26][CH:25]=[N:24][C:23]=5[N:22]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=4)O)=[CH:13][CH:12]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([CH2:18][C:20]4[C:28]5[C:27]([O:29][CH3:30])=[N:26][CH:25]=[N:24][C:23]=5[NH:22][CH:21]=4)=[C:15]([F:17])[N:16]=3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 67445534[6-(6-cyclopropyl-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

Product 1

HCID 54588864HCID 54588864, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To [6-(6-cyclopropyl-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (73, 70 mg, 0.12 mmol) in 10.0 mL of 1,2-dichloroethane, triethylsilane (1.00 mL, 6.26 mmol) and trifluoroacetic acid (0.60 mL, 7.8 mmol) are added and the reaction stirred at 80° C. for 4 hours. The reaction is poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-4004, 11.8 mg). MS (ESI) [M+H+]+=390.9.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8796848b84d1467092b4cfe31169c29d
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

Loading…