Hydrochloric Acid → HCID 11659330, compound

HRID 1435924Notes

Reaction equation

HRID 1435924 reaction equation
C([N:8]1[CH2:20][C@@H:19]2[C@H:10]([C:11](=[O:25])[NH:12][C:13]3[C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)C1C=CC=CC=1.[ClH:26].[H][H]>CO.CCOCC.[Pd]>[ClH:26].[F:24][C:21]([F:22])([F:23])[C:14]1[C:13]2[NH:12][C:11](=[O:25])[C@@H:10]3[CH2:9][NH:8][CH2:20][C@H:19]3[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11560016HCID 11560016, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11659330HCID 11659330, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (±)-trans-2-benzyl-6-(trifluoromethyl)-1,2,3,3a-tetrahydro-5H-pyrrolo[3,4-c]quinolin-4(9bH)-one from Example 5, Part B (30 mg, 0.087 mmol) in 10 mL of methanol was added HCl (0.25 mL of a 2M solution in ether, 0.5 mmol) and 10% Pd/C catalyst (10 mg). The resulting mixture was shaken in a Parr apparatus under 65 psi of hydrogen for 3 h. The reaction was filtered through a pad of Celite and concentrated in vacuo. The resulting solid was triturated several times with ether and dried in vacuo to afford 15 mg (60%) of the title compound of Example 6 as an off-white solid. 1H NMR (DMSO-D6): δ 10.09 (broad s, 1H), 9.90 (broad s, 1H), 9.69 (s, 1H), 7.61 (d, 1H), 7.50 (d, 1H), 7.24 (t, 1H), 3.95-3.88 (m, 1H), 3.52-3.38 (overlapping m, 2H), 3.32-3.20 (overlapping m, 2H), 3.08-2.98 (m, 1H). LRMS (ESI): 257.10 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. customThe resulting solid was triturated several times with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cca97866d3004b21af7392ff2d8ee59d
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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