Acetic Acid → HCID 86677693, compound

HRID 1499762Notes

Reaction equation

HRID 1499762 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:15]([C:17]3[C:18]([O:36][CH2:37][CH3:38])=[C:19]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[N:29][CH:30]=4)[C:20]([CH3:24])=[C:21]([Cl:23])[CH:22]=3)[CH3:16])[N:9]=[C:10]([CH:11]([OH:14])CO)[C:3]=12.C(O)(=O)C.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:15]([C:17]3[C:18]([O:36][CH2:37][CH3:38])=[C:19]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[N:29][CH:30]=4)[C:20]([CH3:24])=[C:21]([Cl:23])[CH:22]=3)[CH3:16])[N:9]=[C:10]([CH:11]=[O:14])[C:3]=12

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23667635Sodium periodateHCID 86677692HCID 86677692, compound

Product 1

HCID 86677693HCID 86677693, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-{1-[4-amino-3-(1,2-dihydroxyethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-5-chloro-2-ethoxy-6-methylphenyl)-N,N-dimethylpyridine-2-carboxamide (70 mg, 0.13 mmol) in tetrahydrofuran (0.98 mL) and water (0.59 mL) was added acetic acid (1.9 μL, 0.034 mmol) and sodium periodate (83 mg, 0.39 mmol) at 0° C. After stirring for 2 h, the reaction mixture was diluted with water, and extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give the desired product (0.059 g, 90%). LCMS calculated for C25H27ClN7O3 (M+H)+: m/z=508.2; Found: 508.1.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-339f01af476e412fb41b6f6b2be5d5d8
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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