Sodium Hydroxide → HCID 24998400, compound

HRID 1096913Notes

Reaction equation

HRID 1096913 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([CH:37]=[C:38]([O:46][CH3:47])[C:39]=1[C:40]1[CH:41]=[N:42][N:43]([CH3:45])[CH:44]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]2([CH2:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:27]4[CH:28]=[N:29][CH:30]=[C:31]([CH:36]=4)[C:32]([O:34]C)=[O:33])[CH:22]=3)[O:17]2)[CH2:13][CH2:12]1)=[O:10])[CH3:4]>CO.C1COCC1>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([CH:37]=[C:38]([O:46][CH3:47])[C:39]=1[C:40]1[CH:41]=[N:42][N:43]([CH3:45])[CH:44]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]2([CH2:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:27]4[CH:28]=[N:29][CH:30]=[C:31]([CH:36]=4)[C:32]([OH:34])=[O:33])[CH:22]=3)[O:17]2)[CH2:13][CH2:12]1)=[O:10])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 24997464HCID 24997464, compound

Product 1

HCID 24998400HCID 24998400, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1 N sodium hydroxide solution (0.75 mL) was added to a solution of Methyl 5-{1′-[3-ethoxy-5-methoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoyl]-4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinate in MeOH (2 ml) and THF (2 ml) and stirred at room temperature for over night. The organic solvent was evaporated and diluted with water. Aqueous 1N HCl aq. (1 ml) was added thereto at room temperature, and the resulted solid was collected and recrystallized from MeOH to afford the intended compound as a colorless solid. 1H-NMR (DMSO-d6) δ: 9.08 (1.0H, d, J=2.2 Hz), 9.02 (1.0H, d, J=1.7 Hz), 8.41 (1.0H, dd, J=2.2, 1.7 Hz), 8.07-8.03 (3.0H, m), 7.88 (1.0H, d, J=0.5 Hz), 7.27-7.24 (1.0H, m), 6.72-6.70 (2.0H, m), 4.33-4.19 (1.0H, br m), 4.09 (2.0H, q, J=7.0 Hz), 3.85 (3.0H, s), 3.83 (3.0H, s), 3.67-3.11 (3.0H, br m), 2.94 (2.0H, s), 2.12-1.89 (2.0H, br m), 1.84-1.77 (2.0H, m), 1.37 (3.0H, t, J=7.0 Hz). MS [M+H]+=597.

Workup

  1. customThe organic solvent was evaporated
  2. additiondiluted with water
  3. additionAqueous 1N HCl aq. (1 ml) was added
  4. customat room temperature, and the resulted solid was collected
  5. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-e28250c795cb408c8dd30241bd39af55
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…