N-{1'-[(4-methoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}acetamide → N-{1'-[(4-methoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}acetamide hydrochloride

HRID 545168Notes

Reaction equation

HRID 545168 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3([CH2:29][C:28](=[O:30])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([NH:31][C:32](=[O:34])[CH3:33])[CH:26]=4)[O:21]3)[CH2:17][CH2:16]2)=[O:14])[CH:4]=1.[ClH:35].CCOC(C)=O>C(Cl)(Cl)Cl.CO>[ClH:35].[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:13]([N:15]2[CH2:16][CH2:17][C:18]3([CH2:29][C:28](=[O:30])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([NH:31][C:32](=[O:34])[CH3:33])[CH:26]=4)[O:21]3)[CH2:19][CH2:20]2)=[O:14])[CH:4]=1

Participants

5

Reactant 2

HCID 16041575N-{1'-[(4-methoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}acetamideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 16041576N-{1'-[(4-methoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}acetamide hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

14.0 g of the compound obtained in Example 1 was dissolved in CHCl3 (80 mL)-MeOH (20 mL), to which was added 4 N HCl/EtOAc (15 mL), and the resulting mixture was concentrated. The residue was dissolved in 30 mL of MeOH, and 50 mL of water was added to it at 0° C., stirred at room temperature for 18 hours. The resulting precipitate was taken out through filtration, washed with 30% MeOHaq and dried in vacuum to obtain the intended compound. 1H-NMR (300 MHz, DMSO-d6) δ: 10.04 (1H, s), 8.24 (1H, d, J=8.5 Hz), 8.09 (1H, d, J=8.3 Hz), 8.01 (1H, d, J=2.7 Hz), 7.96-7.89 (1H, m), 7.77-7.69 (2H, m), 7.38 (1H, s), 7.06 (1H, d, J=8.9 Hz), 4.37-4.26 (1H, m), 4.18 (3H, s), 3.60-3.39 (2H, m), 3.37-3.22 (1H, m), 2.88 (2H, s), 2.13-1.98 (1H, m), 2.02 (3H, s), 1.94-1.75 (3H, m). MS [M+H]+=460.

Workup

  1. concentrationthe resulting mixture was concentrated
  2. dissolutionThe residue was dissolved in 30 mL of MeOH
  3. addition50 mL of water was added to it at 0° C.
  4. filtrationThe resulting precipitate was taken out through filtration
  5. washwashed with 30% MeOHaq
  6. customdried in vacuum
  7. customto obtain the intended compound

Sources & evidence

ORD record
ord-8ed0ec8279814be2a01cace0db57d1b7
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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