Potassium Hydroxide → HCID 86296117, compound

HRID 627066Notes

Reaction equation

HRID 627066 reaction equation
C(OC([N:6]1[CH2:15][CH2:14][C:13]2[C:12]3[NH:16][CH:17]=[CH:18][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>CCO.O>[CH:18]1[C:11]2[S:10][C:9]3[CH2:8][CH2:7][NH:6][CH2:15][CH2:14][C:13]=3[C:12]=2[NH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 90410906HCID 90410906, compound

Product 1

HCID 86296117HCID 86296117, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of the product from step (g) (0.049 g, 0.19 mmol) in EtOH (2 ml) was added 40% aqueous KOH (2 ml). The reaction mixture was heated to 100° C. until LCMS indicated no starting material present (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 LCMS gave the title compound as a tan solid. 1H NMR (CDCl3) δ 8.05 (bs, 1H), 6.95-6.90 (m, 1 H), 6.41-6.36 (m, 1H), 3.10-3.02 (m, 4H), 3.00-2.94 (m, 2 H), 2.92-2.82 (m, 2 H); MS: ESI (positive): 193 (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 LCMS

Sources & evidence

ORD record
ord-55f0d0079f974baca1e5d5e203bd91f1
Source dataset
uspto-grants-2016_04
Patent number
US09309262B2

Reaction notes

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