Sodium Carbonate → HCID 178455121, compound

HRID 1053785Notes

Reaction equation

HRID 1053785 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][N:17]=1)[C:13]#[N:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:19][OH:20].C([O-])([O-])=O.[Na+].[Na+]>CCO>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][N:17]=1)[C:13](=[NH:14])[NH:19][OH:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 583550752-((Tert-butyldimethylsilyloxy)methyl)isonicotinonitrile

Product 1

HCID 178455121HCID 178455121, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Prepared using General Procedure 1. To 2-((tert-butyldimethylsilyloxy)methyl)isonicotinonitrile INT-71 (0.169 g, 0.68 mmol) in EtOH (8 mL) was added hydroxylamine hydrochloride (0.142 g, 2.0 mmol) and Na2CO3 (0.216 g, 2.0 mmol) and the reaction mixture was heated at 85° C. for 12 h. Once cooled to room temperature, the reaction mixture was filtered using EtOH to rinse the filter cake. The filtrate was concentrated under reduced pressure and washed with EA and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated to produce 0.191 g (100%) of 2-((tert-butyldimethylsilyloxy)methyl)-N-hydroxyisonicotinimidamide INT-72 as a light yellow oil. LCMS-ESI (m/z) calculated for C13H23N3O2Si: 281.4; found 282.1 [M+H]+, tR=2.76 min (Method 1). 1H NMR (400 MHz, (CD3)2SO) δ 8.50 (dd, J=5.2, 0.7, 1H), 7.74 (dd, J=1.6, 0.7, 1H), 7.51 (dd, J=5.2, 1.7, 1H), 5.98 (s, 2H), 0.96-0.89 (m, 9H), 0.14-0.07 (m, 6H).

Workup

  1. customPrepared
  2. temperatureOnce cooled to room temperature
  3. filtrationthe reaction mixture was filtered
  4. washto rinse the filter cake
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washwashed with EA and brine
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-53d431679cf349b0ad6c309ed7009fd7
Source dataset
uspto-grants-2016_07
Patent number
US09394264B2

Reaction notes

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