Trifluoroacetic acid → HCID 68523991, compound

HRID 1836569Notes

Reaction equation

HRID 1836569 reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]2[C:15]3=[C:16]([CH2:18][CH2:19][CH2:20][N:14]3[CH2:13][C@@H:12]3[CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][C@H:11]23)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:2]1([NH:1][C:8]2[CH:9]=[C:10]3[C:15]4=[C:16]([CH2:18][CH2:19][CH2:20][N:14]4[CH2:13][C@@H:12]4[CH2:21][NH:22][CH2:23][C@H:11]34)[CH:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23518419HCID 23518419, compound

Product 1

HCID 68523991HCID 68523991, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-cis-tert-butyl 2-anilino-5,6,8a,9,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-10(8H)-carboxylate (80 mg, 0.20 mmol) in 5 ml of CH2Cl2 was added 1 ml of trifluoroacetic acid and the reaction was stirred at room temperature for 3 h. The volatiles were removed under reduced pressure and the residue was purified by prep HPLC (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA). Product-containing fractions were combined, concentrated and partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo to afford 15 mg (23%) of the title compound of EXAMPLE 17. 1H NMR (CDCl3): δ 7.18 (app t, 2H, J=7.8 Hz), 6.84 (app d, 2H, J=8.0 Hz), 6.78-6.72 (m, 1H), 6.67 (s, 1H), 6.65 (s, 1H), 5.46 (s, 1H), 3.45-3.30 (m, 2H), 3.24-3.17 (m, 1H), 3.08-3.00 (m, 2H), 2.97-2.85 (m, 1H), 2.78-2.55 (broad m, 6H), 2.05-1.93 (m, 2H). LRMS (ES)+: 306.3 (M+H)+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by prep HPLC (
  3. washC18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA)
  4. concentrationconcentrated
  5. custompartitioned between chloroform and saturated aqueous sodium carbonate
  6. washThe organics were washed with brine
  7. dry with materialdried (K2CO3)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2e47dc21e44d728938c8dcc2e45e53
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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