Trifluoroacetic acid → HCID 16062137, compound

HRID 1917255Notes

Reaction equation

HRID 1917255 reaction equation
C(OC([N:8]1[CH2:31][CH2:30][C:11]2[N:12]=[C:13]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:23]([C:13]1[N:14]=[C:15]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:10]2[CH2:9][NH:8][CH2:31][CH2:30][C:11]=2[N:12]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66618430HCID 66618430, compound

Product 1

HCID 16062137HCID 16062137, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Step B (0.131 g, 0.312 mmol) in CH2Cl2 was treated with TFA. After stirring for 4 h, the mixture was concentrated and partitioned between saturated (satd.) aq. NaHCO3 and CH2Cl2 (2×). The combined organic layers were dried and concentrated. The resulting residue was purified via SiO2 chromatography (1-7% 2 M NH3 in MeOH/CH2Cl2) to give 0.084 g (84%) of the title compound. MS (ESI): exact mass calcd. for C20H18FN3, 319.15; m/z found, 320.4 [M+H]+. 1H NMR (CDCl3): 7.51 (dd, J=5.4, 8.8, 2H), 7.41 (d, J=7.4, 2H), 7.31-7.27 (m, 2H), 7.22-7.19 (m, 1H), 7.15 (dd, J=8.7, 2H), 4.27 (s, 2H), 3.95 (s, 2H), 3.24 (t, J=6.1, 2H), 2.97 (t, J=6.1, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. custompartitioned between saturated (satd.) aq. NaHCO3 and CH2Cl2 (2×)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe resulting residue was purified via SiO2 chromatography (1-7% 2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4dcfd2556bdf4936976a3991f506a9ff
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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