Trifluoroacetic acid → HCID 25071628, compound

HRID 1027876Notes

Reaction equation

HRID 1027876 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]3[CH2:20][CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:18]=3[N:17]=[C:16]([NH2:29])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:11]1([C:14]2[C:19]3[CH2:20][CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:18]=3[N:17]=[C:16]([NH2:29])[N:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69225680HCID 69225680, compound

Product 1

HCID 25071628HCID 25071628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 30A (38 mg, 0.096 mmol) in CH2Cl2 (1 mL) was treated with TFA (2 mL), heated at 60° C. for 2 minutes, cooled, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of 2, 3.5, 5 and 10% (9:1 MeOH: saturated aqueous NH4OH) in CH2Cl2 to provide the title compound. 1H NMR (CDCl3) δ 2.72 (t, J=5.93 Hz, 2H), 2.91-3.09 (m, 4H), 3.26-3.46 (m, 4H), 4.54 (t, J=5.93 Hz, 2H), 4.79 (s, 2H), 7.09 (dd, J=7.97, 1.19 Hz, 1H), 7.17-7.26 (m, 1H), 7.34-7.41 (m, 1H), 7.89 (dd, J=7.63, 1.86 Hz, 1H); MS (M+H)+ m/z 298.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customchromatographed on silica gel eluting with a gradient of 2, 3.5, 5 and 10% (9:1 MeOH: saturated aqueous NH4OH) in CH2Cl2

Sources & evidence

ORD record
ord-6ea9dedaad8c485cbbbdeacd26fb46be
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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