Potassium Hydroxide → HCID 78426199, compound

HRID 627068Notes

Reaction equation

HRID 627068 reaction equation
C(OC([N:6]1[CH2:15][CH2:14][C:13]2[C:12]3[N:16]([CH2:19][CH3:20])[CH:17]=[CH:18][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>CCO.O>[CH2:19]([N:16]1[C:12]2[C:13]3[CH2:14][CH2:15][NH:6][CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[CH:18]=[CH:17]1)[CH3:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 90411361HCID 90411361, compound

Product 1

HCID 78426199HCID 78426199, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of the product from step (a) (0.060 g, 0.21 mmol) in EtOH (2 ml) was added 40% aqueous KOH (2 ml). The reaction mixture was heated to 100° C. until LCMS indicated that the reaction was complete (usually 16-32 hours). The reaction mixture was cooled to RT, diluted with water (30 ml), and extracted with DCM (3×). The combined DCM extracts were dried (MgSO4), filtered, and solvent evaporated in vacuo to give the crude product. Purification by preparative HPLC gave the title compound as a tan solid. 1H NMR (CD3)2CO™ 6.82 (d, J=2.7 Hz, 1H), 6.14 (d, J=2.7 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 3.01-2.92 (m, 6H), 2.86-2.78 (m, 2H), 1.35 (t, J=7.2 Hz, 3H); MS: ESI (positive): 221 (M+H).

Workup

  1. customusually 16-32 hours
  2. temperatureThe reaction mixture was cooled to RT
  3. extractionextracted with DCM (3×)
  4. dry with materialThe combined DCM extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customsolvent evaporated in vacuo
  7. customto give the crude product
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-20cf727ad7be416ab8048e82d49a9ab5
Source dataset
uspto-grants-2016_04
Patent number
US09309262B2

Reaction notes

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