HCID 18785837, compound → HCID 18785886, compound

HRID 1107729Notes

Reaction equation

HRID 1107729 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:4]=1.[H][H]>CO.Cl.[Pt]=O>[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:4]=1

Participants

6

Reactant 2

HCID 18785837HCID 18785837, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18785886HCID 18785886, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

A slurry of platinum oxide (8 mg, 10 moll) in methanol (1 ml) was added to a solution of 1-amino-3-(4-pyridyl)-3,4-dihydroisoquinoline hydrochloride (Example 28) (150 mg, 0.578 mmol) in methanol and concentrated hydrochloric acid (0.4 ml), and stirred under 3 atmospheres of hydrogen for 16 h. The mixture was filtered through celite and evaporated. The residue was purified by RP-HPLC to yield a white hygroscope solid (126 mg). [M+H]+ 230; 360 MHz 1H n.m.r (d6 -DMSO) 10.30 (1H, s), 9.43 (1H, s), 9.03 (1H, s), 8.80 (1H, br.s), 8.56 (1H, br.s), 8.05 (1H, d, J 7.8 Hz), 7.71 (1H, t, J 7.5 Hz), 7.54-7.50 (2H, m), 3.72-3.68 (1H, m), 3.27 (2H, d, J 13.2 Hz), 3.15 (1H, dd, J 17, 4 Hz), 2.99 (1H, dd, J 17.2, 6.9 Hz), 2.80-2.74 (2H, m), 1.95-1.63 (3H, m), 1.48-1.38 (2H, m).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated
  3. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-cb7ce2f235754b7c9370ef8e564ab726
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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