Water → HCID 67410299, compound

HRID 1913465Notes

Reaction equation

HRID 1913465 reaction equation
O.OO.N[C:5]([NH2:7])=[O:6].[OH-].[Na+].[C:10]([O:14][C:15]([N:17]1[CH2:42][CH2:41][C:20]2([CH2:23][N:22]([C@H:24]3[C:32]4[C:27](=[CH:28][C:29]([C:33]5[CH:34]=[N:35][C:36](C#N)=[CH:37][CH:38]=5)=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[CH2:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CCO>[C:10]([O:14][C:15]([N:17]1[CH2:42][CH2:41][C:20]2([CH2:23][N:22]([C@H:24]3[C:32]4[C:27](=[CH:28][C:29]([C:33]5[CH:34]=[N:35][C:36]([C:5](=[O:6])[NH2:7])=[CH:37][CH:38]=5)=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[CH2:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31294Carbamide PeroxideHCID 67409002HCID 67409002, compound

Product 1

HCID 67410299HCID 67410299, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of water (150 mL) and urea hydrogen peroxide (916 mg, 9.45 mmol) was added sodium hydroxide (220 mg, 5.51 mmol) and the reaction was stirred at room temperature. Once a clear solution was obtained, the reaction was placed in an ice bath and fitted with an addition funnel. A solution of 2-[(R)-5-(6-cyano-pyridin-3-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester (4-1c, 700 mg, 1.58 mmol) in 50 mL EtOH was added dropwise via the funnel over 30 minutes. The reaction was warmed to room temperature and was stirred overnight. The reaction mixture (a white suspension) was filtered and the solids were washed with 50 mL water and air-dried to give 440 mg (60%) of the title compound as an off-white powder. MS (ES+) 463.1 (M+H)+. 1H NMR (DMSO-d6) δ 1.39 (s, 9H), 1.54-1.62 (m, 4H), 1.81-1.91 (m, 1H), 2.06 (dd, 1H), 2.76-2.87 (m, 1H), 2.94-3.02 (m, 3H), 3.10 (d, 2H), 3.24 (br s, 4H), 3.86 (dd, 1H), 7.40 (d, 1H), 7.55 (d, 1H), 7.62-7.68 (m, 2H), 8.09 (d, 1H), 8.12 (br s, 1H), 8.22 (dd, 1H), 8.89 (d, 1H).

Workup

  1. customOnce a clear solution was obtained
  2. customthe reaction was placed in an ice bath
  3. customfitted with an addition funnel
  4. temperatureThe reaction was warmed to room temperature
  5. stirringwas stirred overnight
  6. filtrationThe reaction mixture (a white suspension) was filtered
  7. washthe solids were washed with 50 mL water
  8. customair-dried

Sources & evidence

ORD record
ord-2d518a862a5945fd87b35e937313f7f1
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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