Hydrochloric Acid → HCID 131724543, compound

HRID 1836585Notes

Reaction equation

HRID 1836585 reaction equation
[O:1]=[C:2]1[C@@H:11]2[CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][C@@H:10]2[C:9]2[C:4]3=[C:5]([CH2:22][CH2:23][N:3]13)[CH:6]=[CH:7][CH:8]=2.FC(F)(F)C(O)=O.CCOCC.[ClH:36]>C(Cl)Cl.C(O)C>[ClH:36].[CH:8]1[CH:7]=[CH:6][C:5]2[CH2:22][CH2:23][N:3]3[C:4]=2[C:9]=1[C@H:10]1[CH2:14][NH:13][CH2:12][C@H:11]1[C:2]3=[O:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 6422Trifluoroacetic acidHCID 131724544HCID 131724544, compound

Product 1

HCID 131724543HCID 131724543, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-cis tert-butyl 7-oxo-4,5,7a,8,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline-9(7H)-carboxylate (100 mg, 0.32 mmol) in 5 mL of methylene chloride was added trifluoroacetic acid (1 mL). This mixture was stirred at ambient temperature for 2 h and then concentrated in vacuo. The residue was basified with sat'd aq Na2CO3 and extracted with chloroform. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo to afford the free base. This residue was dissolved in 1 mL absolute ethanol and 5 mL ether and then 2M HCl in ether (0.32 mL, 0.64 mmol) was added and a solid fell out of solution. The solvents were decanted and the solid was triturated twice with ether and dried in vacuo to afford 40 mg (50%) of the title compound of EXAMPLE 108 as an off white powder. 1H NMR (dmso-D6) δ: 9.42 (broad s, 1H), 9.20 (broad s, 1H), 7.16 (app t, 2H, J=8.0 Hz), 6.97 (app t, 1H, J=7.5 Hz), 4.05-3.95 (m, 3H), 3.79-3.70 (m, 1H), 3.68-3.53 (m, 2H), 3.51-3.42 (m, 1H), 3.20-3.10 (m, 2H), 2.90-2.80 (m, 1H). LRMS (ES)+: 214.9 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with chloroform
  3. washThe organics were washed with brine
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo
  6. customto afford the free base
  7. customThe solvents were decanted
  8. customthe solid was triturated twice with ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-880005cb450e4d3f9c3c62ec93568b57
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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