Potassium Hydroxide → HCID 86295479, compound

HRID 627070Notes

Reaction equation

HRID 627070 reaction equation
C(OC([N:6]1[CH2:15][CH2:14][C:13]2[C:12]3[N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[CH:18][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>CCO.O>[C:19]1([N:16]2[C:12]3[C:13]4[CH2:14][CH2:15][NH:6][CH2:7][CH2:8][C:9]=4[S:10][C:11]=3[CH:18]=[CH:17]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 90410529HCID 90410529, compound

Product 1

HCID 86295479HCID 86295479, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of the product from step (a) (0.066 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 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. 1HNMR (CD3)2CO™ 7.52-7.50 (m, 2H), 7.44-7.41 (m, 3H), 6.97 (d, J=3 Hz, 1H), 6.42 (d, J=3 Hz, 1H), 2.92-2.89 (m, 4H), 2.74-2.71 (m, 2H), 2.52-2.49 (m, 2H), 2.06-2.04 (m, 1H); MS: ESI (positive): 269 (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-33dcdf24656a413a84027df5b0065870
Source dataset
uspto-grants-2016_04
Patent number
US09309262B2

Reaction notes

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