Trifluoroacetic acid → HCID 15982220, compound

HRID 1367286Notes

Reaction equation

HRID 1367286 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-f557a00ee7d04c2aaae1bc48df0de500
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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