Trifluoroacetic acid → HCID 16666254, compound

HRID 2366480Notes

Reaction equation

HRID 2366480 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[NH:9][C:8]=2[CH:7]=[C:6]([F:32])[CH:5]=1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[F:32][C:6]1[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]4)=[CH:15][CH:14]=3)[NH:9][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90925078HCID 90925078, compound

Product 1

HCID 16666254HCID 16666254, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of EXAMPLE 88C (0.26 g, 0.6 mmol) in dichloromethane (5 mL) was treated with trifluoroacetic acid (5 mL) and the mixture stirred at ambient temperature for 4 hours. The mixture was concentrated and purified by flash chromatography on silica gel using 0-10% methanol/dichloromethane/0.1% ammonium hydroxide, followed by HPLC on a C18 column using 0-100% acetonitrile/water/0.1% trifluoroacetic acid, to provide the title compound (0.131 g) as the trifluoroacetate salt. 1HNMR (DMSO-D6) δ 9.22 (s, 1H), 8.63 (s, 1H), 8.38 (s, 1H), 8.21 (d, J=8.3 Hz, 2H), 7.94 (s, 1H), 7.55-7.62 (m, 2H), 7.45 (t, J=7.7 Hz, 2H), 3.40 (s, 2H), 2.99-3.07 (m, 2H), 1.99 (s, 2H), 1.78-1.90 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography on silica gel using 0-10% methanol/dichloromethane/0.1% ammonium hydroxide

Sources & evidence

ORD record
ord-da04355023aa4b3db8372344d6cc586f
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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