Trifluoroacetic acid → HCID 24956038, compound

HRID 1952109Notes

Reaction equation

HRID 1952109 reaction equation
C(OC(=O)[N:7]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[C:10]([Cl:25])[N:9]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[NH:17]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:23]2[C:15]([CH2:14][C:11]2[CH:12]=[CH:13][C:8]([NH:7][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)=[N:9][C:10]=2[Cl:25])=[CH:16]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58442093HCID 58442093, compound

Product 1

HCID 24956038HCID 24956038, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (4-chloro-benzyl)-6-chloro-5-[hydroxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl-carbamic acid tert-butyl ester (542, 1.00 g, 2.00 mmol) in acetonitrile (130.0 mL) were added triethylsilane (11.5 mL, 0.0720 mol) and trifluoroacetic acid (5.5 mL, 0.071 mol). The reaction was heated to reflux for 2 hours, then concentrated, poured into aqueous potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and washed with ethyl acetate and hexane to give a light yellow solid (P-0161, 480 mg, 62%). MS (ESI) [M+H+]+=383.1, 385.1.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. additionpoured into aqueous potassium carbonate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. washwashed with ethyl acetate and hexane
  10. customto give a light yellow solid (P-0161, 480 mg, 62%)

Sources & evidence

ORD record
ord-9383139ea83f4e4fa48e2d88cb92664b
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

Loading…