Trifluoroacetic acid → HCID 15982220, compound

HRID 1256730Notes

Reaction equation

HRID 1256730 reaction equation
C(OC(=O)[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25](O)[C:26]2[C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[C:21]([CH3:36])[N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.C(OC(=O)N(C1C=CC(C(OC)C2C3C(=NC=CC=3)NC=2)=C(C)N=1)CC1C=CC(C(F)(F)F)=CC=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[CH3:36][C:21]1[N:20]=[C:19]([NH:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=2)[CH:24]=[CH:23][C:22]=1[CH2:25][C:26]1[C:34]2[C:29](=[N:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 66970774HCID 66970774, compoundHCID 66971161HCID 66971161, compound

Product 1

HCID 15982220HCID 15982220, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

The combined materials of {5-[Hydroxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-6-methyl-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (37) and {5-[Methoxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-6-methyl-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (38) (194 mg, 0.378 mmol) were dissolved in acetonitrile (3 mL) and triethylsilane (0.30 mL, 1.9 mmol) and trifluoroacetic acid (0.17 mL, 2.3 mmol) were added. After stirring at 25° C. for overnight, TLC analysis indicated that the reaction was about 50% complete. To the reaction mixture was added triethylsilane (0.30 mL, 1.9 mmol), and trifluoroacetic acid (0.17 mL, 2.3 mmol). The mixture was allowed to stir for another 48 hours at 25° C. and the solvent, excess triethylsilane and trifluoroacetic acid were removed by evaporation. Ethyl acetate was added and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford a brown oil. Purification of 80 mg of the crude material was carried out using preparatory chromatography (50% ethyl acetate in hexanes) to afford the compound as an off-white solid (P-0013, 10 mg, 0.025 mmol). MS (ESI) [M+H+]+=397.2.

Workup

  1. stirringto stir for another 48 hours at 25° C.
  2. customthe solvent, excess triethylsilane and trifluoroacetic acid were removed by evaporation
  3. additionEthyl acetate was added
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customto afford a brown oil
  9. customPurification of 80 mg of the crude material

Sources & evidence

ORD record
ord-68f84388b8e14bfca7d7dac7a3e20c2d
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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