Trifluoroacetic acid → HCID 10047632, compound

HRID 860996Notes

Reaction equation

HRID 860996 reaction equation
C([O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[C:23]([C:31]([S:34]([CH3:37])(=[O:36])=[O:35])([CH3:33])[CH3:32])[CH:24]=[C:25]4[C:30]=3[N:29]=[CH:28][CH:27]=[CH:26]4)[CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:37][S:34]([C:31]([C:23]1[CH:24]=[C:25]2[C:30](=[C:21]([C:17]3[CH:16]=[C:15]([C:12]4[CH:11]=[CH:10][C:9](=[O:8])[NH:14][CH:13]=4)[CH:20]=[CH:19][CH:18]=3)[CH:22]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)([CH3:33])[CH3:32])(=[O:35])=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69374133HCID 69374133, compound

Product 1

HCID 10047632HCID 10047632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[3-(6-Benzyloxy-pyridin-3-yl)-phenyl]-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline from Step 2 (1.0 eq.) in CH2Cl2 (0.2M) was added an equi volume of TFA. The mixture was stirred for 72 h, concentrated, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2:MeOH; 95:5) afforded the title compound as a light yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 8.95 (dd, 1H), 8.53 (d, 1H), 8.28 (d, 1H), 8.04 (d, 1H), 7.89 (dd, 1H), 7.79 (s, 1H), 7.75 (s, NH), 7.63–7.53 (m, 4H), 6.46 (d, 1H), 2.82 (s, 3H), 1.94 (s, 6H).

Workup

  1. concentrationconcentrated
  2. additionpoured in saturated aqueous NaHCO3
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29a15576fade42e4bb17da4201926db4
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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