HCID 69055020, compound → HCID 11492299, compound

HRID 2100596Notes

Reaction equation

HRID 2100596 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][C@H:8]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C@@H:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.ClC1C2C(=O)N[C@@H]3CN(C(OC(C)(C)C)=O)C[C@H]3C=2C=CC=1.[H][H]>CO.C(O)(=O)C.[Pd]>[ClH:1].[CH2:15]1[C@H:7]2[C@@H:8]([NH:9][C:10](=[O:12])[C:11]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=32)[CH2:13][NH:14]1

Participants

7

Reactant 3

HCID 69055020HCID 69055020, compoundHCID 69060793HCID 69060793, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11492299HCID 11492299, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3aR,9bS)-tert-butyl 6-chloro-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from Example 27, Part B (10 mg) in methanol was added 2 drops of acetic acid and 2 mg of 10% Pd/C catalyst. The mixture was shaken under 70 psi of hydrogen on a Parr shaker for 3 h. The mixture was filtered through a pad of Celite and concentrated in vacuo. The residue was taken up in 2 mL of methanol and then there was added 1 mL of 12 N HCl. The reaction was stirred at ambient temperature for 10 min and then was concentrated in vacuo at 60° C. to afford 7 mg of the title compound of Example 32 as an off-white solid. 1H NMR (CD3OD): 7.92 (d, 1H), 7.51 (app t, 1H), 7.39 (app t, 1H), 7.18 (d, 1H), 4.02-3.95 (m, 1H), 3.76-3.70 (m, 1H), 3.66-3.61 (m, 1H), 3.58-3.52 (m, 1H), 3.41-3.30 (overlapping m, 2H). LRMS (ESI): 189 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. additionthere was added 1 mL of 12 N HCl
  4. concentrationwas concentrated in vacuo at 60° C.

Sources & evidence

ORD record
ord-c32a389b5c584ae2b84f2e2e64e8b4f1
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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