Sodium Hydroxide → HCID 86595423, compound

HRID 971159Notes

Reaction equation

HRID 971159 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[C:10](=[O:33])[C:9]=2[N:8]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[N:7]=1)=O)C.[OH-].[Na+]>CCO>[C:29]([O:28][C:26](=[O:27])[N:24]([C:21]1([C:18]2[CH:17]=[CH:16][C:15]([N:11]3[CH2:12][CH2:13][C:14]4[C:6]([CH:4]=[O:3])=[N:7][N:8]([C:34]5[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=5)[C:9]=4[C:10]3=[O:33])=[CH:20][CH:19]=2)[CH2:22][CH2:23]1)[CH3:25])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69516572HCID 69516572, compound

Product 1

HCID 86595423HCID 86595423, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part A. 6-{4-[1-(tert-Butoxycarbonyl-methyl-amino)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.59 g, 1.79 mmol) was stirred in EtOH (15 mL) and 1N NaOH (3 mL) at rt for 1 h. After evaporation, the mixture was acidified with citric acid. The mixture was extracted with EtOAc (2×), washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness in vacuo. This acid underwent a series of reactions similar to those used in Part E of Example 1 to afford (1-{4-[3-formyl-1-(4-methoxy-phenyl)-7-oxo-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-phenyl}-cyclopropyl)-methyl-carbamic acid tert-butyl ester (yield: 99%). LC/MS (ESI+) 461.6 (M+H−t-Bu)+, tR=1.2.97 min (10–90% CH3CN/H2O in a 4-min run).

Workup

  1. customAfter evaporation
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-a35f5314d56641fda22c14907f58e4d1
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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