Trifluoroacetic acid → HCID 73009272, compound

HRID 2265770Notes

Reaction equation

HRID 2265770 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][F:36])=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)C)(C)(C)C>ClCCl>[F:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH:23]=[CH:22][C:19]2[CH:20]=[CH:21][C:16]([NH:14][CH3:13])=[CH:17][CH:18]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86609321HCID 86609321, compound

Product 1

HCID 73009272HCID 73009272, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 ml) was added slowly to a solution of compound 11a (7.0 mg, 0.017 mmol) in dichloromethane (1 ml). The mixture was then stirred at room temperature for 1 hour. After standard workup with dichloromethane, the residue was purified by silica gel preparative TLC (1.0% methanol in dichloromethane) to afford 12a (3 mg, 56%): 1H NMR δ 7.37 (m, 4H), 6.90 (m, 4H), 6.65 (d, 2H, J=8.4 Hz), 4.60 (d, t, 2H, J1=46 Hz, J2=4.0 Hz), 4.17 (t, 2H), 3.90 (t, 3H), 3.76 (t, 1H), 2.88 (s, 3H). Anal. (C19H22FNO2) C. H. N.

Workup

  1. customAfter standard workup with dichloromethane, the residue was purified by silica gel preparative TLC (1.0% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1082f9a3f947471383e3350906e5c516
Source dataset
uspto-grants-2010_12
Patent number
US07858072B2

Reaction notes

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